2-Iodobenzaldehyde

white to light beige low melting crystalline

General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol, ), (CFPCC (415mg, 1.93mmol, 1.2equiv.) and celite (1.75g) were dried under vacuum in 2-neck-flask and then flushed with nitrogen. After suspension in 19.3mL of dry DCM, a solution of o-iodobenzyl alcohol (14) (390mg, 1.60mmol, 1.0equiv.) in dry DCM (5.33mL) was added drop wise at room temperature. The reaction mixture turns from red to brown and then black, and is stirred at ambient temperature overnight. After filtration through celite, the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (short column, eluent Hexanes/EtOAc=9/1), yielding 367mg (98percent) of aldehyde 15. (0055) R2-Iodobenzaldehvde (19); A suspension of pyridinium chlorochromate (8.28 g, 38.4 mmol) and dry celite (5.00 g) in dry dichloromethane was stirred at room temperature for 15 min. 2-Iodobenzyl alcohol (3.03 g, 12.9 mmol) in dry dichloromethane (50 ml) was added. The suspension was shielded from light and stirred at room temperature for 2 h after which it was diluted with ether, and filtered through celite. The cloudy brown filtrate was concentrated to a red- brown gummy solid which was dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. The solution was concentrated to give 2- iodobenzaldehyde (19) as a pale yellow oil (2.87 g, 95percent). 1H nmr (400 MHz, CDC13): 87. 29 (Td, J 8. 0, 1. 8 Hz, 1H) H4, H6; 7.46 (brt, J 8. 0 Hz, 1H) H5, 7. 88 (dd, J8. 0, 1. 8 Hz, 1H) H6; 7.95 (d, J 8.0 Hz, 1H) H3; 10.07 (s, 1H) CHO.2- iodo- benzyl alcohol ( 2 - iodobenzylalcohol ) ( 10 g , 42.73 mmol ) and dichloromethane ( Dichloromethane ) in 200 mLAfter mixing and put into a pyridine -chloro formate ( pyridium chlorochromate ) ( 10.13 g , 47 mmol ) was stirred at room temperature .After the reaction was completed the solvent was removed and column chromatography (ethyl acetate ( ethyl acetate ) : hexane ( hexane ) =1: 8) to perform , to give a yellow liquid The compound 23-2 ( 2 - iodobenzaldehyde ) ( 9.1g , 92percent)Synthesis of Intermediate 1-(2) (0183)10 g(42.73 mmol) of 2-iodobenzylalcohol was added to 200 mL of dichloromethane, 10.13 g (47 mmol) of pyridine chlorochromate (PCC) was added thereto, and was then stirred at room temperature. When the reaction was complete, the solvent was removed, and column chromatography (ethyl acetate: hexane=1:8) was used to obtain 9.1 g of Intermediate 1-(2) (2-iodobenzaldehyde) as a yellow liquid (yield: 92percent). (0184)1H NMR (300 MHz, CDCl3): δ (ppm) 10.09 (s, 1H), 7.94 (dd, J=15.0, 7.2 Hz, 2H), 7.48 (s, 1H), 7.30 (s, 1H) (0185) A molecular weight for CPreparation Example 63: Synthesis of 2-iodobenzenealdehydeIn a flask, 2-iodobenzyl alcohol (4g, 17.09mmol) was dissolved in dichloromethane (MC, 85ml), and then, manganese oxide (Mn0Preparation Example 63Preparation Example 63Preparation Example 63 In a flask, 2-iodobenzyl alcohol (4g, 17.09mmol) was dissolved in dichloromethane (MC, 85ml), and then, manganese oxide (Mn0Preparation example 16: 2-Iodobenzenealdehyde In a flask, 2-.iodobenzyl alcohol (4g, 17.09mmo 1 ) was dissolved in dichloromethane (MC, 85ml), and then, manganese oxide ( M11O2 , 14.86g, 170.92mmol) was added thereto. The obtained reaction product was stirred under reflux. When the reaction was completed, the obtained reaction product was cooled to room temperature, and then, filtered and concentrated using celite, to obtain the title compound (3.6g, yield 75~90percent) . lH NMR (400MHz, CDC 13) δ 7.30~7.99(m, 4H), lO.HXs, 1H)To a THF solution (16 mL) of commercially available o-iodobenzoicacid (4.15 g, 16.8 mmol) was added boran–dimethylsulfide complex (1.90 mL, 20.0 mmol) at 0°C. After stirring for 15 h at room temperature, phosphate buffer (pH 7) was added. Organic materials were extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, o-iodobenzylalcohol (3.84 g, 98 percent) was obtained as a white solid and used for the next step without further purification. To a DCM suspension (33 mL) of manganese(IV) oxide (14.0 g, 161 mmol) was added the crude o-iodobenzylalcohol (3.77 g, 16.1 mmol). After stirring for 30 h at room temperature, the resulting suspension was filtrated through a small pad of celite using DCM as an eluent. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate 5:1) to give o-iodobenzaldehyde (3.36 g, 90percent) as pale yellow crystals.General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product.General procedure: In a 150 mL thick-walled pressure tube equipped with a magnetic stirrer, In an air atmosphere, To the system was added benzyl alcohol (i.e., R1 in formula (I) H) 1.0 mmol (108.1 mg)Ammonia (1.6 x 10-2 mol / L) 5.0 mL, 5 molpercent (9.5 mg) of cuprous iodide, TEMPO 5 molpercent (7.8 mg), 100 & lt; 0 & gt; C for 12 h, After the reaction is over, The reaction solution was cooled to room temperature, And extracted with ethyl acetate (3 x 5.0 mL). The organic layers were combined and concentrated in vacuo to remove ethyl acetate to give the crude product. The crude product was purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure desired product.The yield of 97.6 mg was 92percent.General procedure: A 25 mL round-bottomed flask was charged with alcohol (1 mmol), 3D-RGO/ZnO (40 mg) and N, N-dimethyl formamide (5 mL). The resultant mixture was stirred under O2 with two white LED lamps (12W). After completion of the reaction, the 3D-RGO/ZnO catalyst was recycled by filtration and the organic phase of the filtrate was extracted with EtOAc, washed three times with water and dried over Na2SO4.The pure product was then isolated by silica chromatography using petroleum ether/EtOAc mixtures as the eluent.Equipped with a magnetic stirrer in round bottom flask methyl benzyl alcohol (12. 22g, 100. Ommol, namely formula The R1 is 4-methyl, R2 is hydrogen, X is carbon, η is 1, m is 0), ferric chloride (0. 81g, 5mmol), L- isoleucineAcid (1.31g, 10mmol), TEMP0 (1.56g, 10mmol), toluene 300. OmL was added , then the reaction with oxygen in the air bottleReplacement, stirred and reflux for 6h. After completion of reaction, the reaction mixture was cooled to room temperature, filtered, the filtrate evaporated to give the crude product, The resultant crude product was purified by column chromatography, with n-hexane: Elution: (10 1 volume ratio) mixed liquid of ethyl acetate containing the desired collectionLabeled compound of the eluent, evaporation of the solvent and dried to give the product p-tolualdehyde 10. 93g, 91percent yield. The reactants adjacent iodobenzene methanol (2. 34g, 10. Ommol, i.e., of formula (I), R1 is iodo, R 2 isHydrogen, X is carbon, [eta] is 1, m is 0) is taken, experimental methods and procedures were the same as in Example 1, except that: ferrous trifluoromethanesulfonate(0 · 35g, 1. Ommol), 4- methoxyphenyl Glycine (0 · 18g, 1 · Ommol), TEMPO (0 · 16g, 1 · Ommol), tert-amyl alcohol 30. OmL, oxygen the reaction was stirred at reflux bottle of air displacement 24h. To give the final product 1. 97g, yield 85percent.General procedure: Alcohol (0.5 mmol), salophen copper (II) complex (2 molpercent), NaOH (0.6 equiv), and 70percent TBHP in water (1.1 equiv) were dissolved in acetonitrile (5 mL), and the homogeneous solution was stirred at room temperature in air overnight. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified over silica gel by column chromatography (10–25percent EtOAc in hexane).General procedure: A vial was charged with alcohol (1 mmol), IBX (1.2 mmol, 1.2 equiv) and 2 wt percent GMPGS-2000/HIn a 25 ml Kjeldahl flask equipped with a magnetic stirrer and a reflux condenser, 2.30 g (9.8 mmols) of o-iodobenzyl alcohol and 5 ml of (87 mmols) of acetic acid were charged and an aqueous solution prepared by dissolving 0.50 g (3.33 mmols) of sodium bromate in 3 ml of water was added dropwise over 2 hours under stirring. In a flask, 2-iodobenzyl alcohol (4g, 17.O9mmol) was dissolved in dichioromethane (MC, 85m1), and then, manganese oxide (Mn02, 14.86g, 170.92mmol) was added thereto. The obtained reaction product was stirred under reflux. When the reaction was completed, the obtained reaction product was cooled to room temperature, and then, filtered and concentrated using celite, to obtain the titlecompound (3.6g, yield 75r’9Opercent).General procedure: A mixture of 2-(2-methoxyphenyl)-1, 3-dithiane (1c) (0.11 g, 0.50mmol), 1, 4-benzoquinone (64.8 mg, 0.60 mmol), and NaI (0.70 mg, 0.005 mmol) in MeCN (2mL) and H

Molecular Weight:232.02
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:231.93851
Monoisotopic Mass:231.93851
Topological Polar Surface Area:17.1
Heavy Atom Count:9
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes