3-(4-BROMO-PHENYL)-PROPIONALDEHYDE

Synthesis of 3-(4-bromophenyl)propanal (10*) Alcohol 4* (4.71g, 21.8mmol) was dissolved in DCM, treated with Dess-Martin periodinane (9.71g, 20.9mmol) and stirred at rt for 2h. The mixture was quenchedwith 2M NaOH, the phases were separated the aqueous layer extracted with DCM. The combined organic phases were dried on Mg504, filtered and evaporated in vacuo. The crude was purified by flash chromatography on silica gel using a gradient of DCM in cHex to yield the desired product 10* (4.46g, 96percent) as a colourless liquid.1H NMR (400MHz, CDCI3) 6 9.81 (5, 1H), 7.41 (d, 2H), 7.07 (d, 2H), 2.91 (t, 2H), 2.79-2.74 (m, 2H).MS (ES) C9H9BrO requires: 211/213, (Mi-H) not found, 100percent.Oxalyl chloride (0.599 mL, 6.973 mmol) was dissolved in DCM (15 mL), and DMSO (0.99 mL, 13.94 mmol)dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirred for 15 minutes, and 3-(4-bromophenyl)propan-1-ol (1.0 g, 4.64 mmol) dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirredfor 30 minutes, and TEA (1.96 mL) was slowly added thereto at -78°C. The temperature was slowly increased to roomtemperature, and the reaction solution was stirred for 3 hours. After termination of the reaction, the reaction solutionwas diluted with water and extracted with DCM. The organic layer was dried with anhydrous magnesiumsulfate andpurified by column chromatography (eluent, EtOAc/Hex = 1/5) to obtain the title compound (0.859 g, 86percent).NMR: 1H-NMR (CDCl3) δ 9.81(1H, s), 7.40 (2H, d), 7.07(2H, d), 2.91(2H, m), 2.77(2H, t)3-(4-Bromophenyl) propan-1-ol (4 g, 18.5 mmol, 1.0 equiv) was dissolved into dichloromethane (60 mL) and cooled to 0°C. PCC (5.21 g, 24.1 mmol, 1.5 equiv) was added in portions and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite bed and the filtrate was concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (10-20 percent diethyl ether/n-pentane) to afford the desired product 5.21a (3.05 g, 76.9 percent yield). 1H NMR (400 MHz, CDCI3) 69.83 (s, 1H), 7.43 (d, J = 8.3 Hz, 2H), 7.10 (d, J 8.2 Hz, 2H), 2.94 (t, J 7.3 Hz, 2H), 2.79 (t, J 7.4 Hz, 2H).To a 0° C. mixture of 26A (7 g, 32.5 mmol) and NaHCOUnder a nitrogen atmosphere, compound (T-19) (50.0 g), allyl alcohol (24.2 mL)), palladium acetate (0.794 g), sodium hydrogencarbonate (44.5 g) and tetrabuthyl ammonium chloride (TBAC) (54.0 g) were put in a reaction vessel, and the resulting mixture was stirred at 40°C for 8 hours. The resulting reaction mixture was poured into water, and the resulting aqueous layer was subjected to extraction with ethyl acetate. Then, organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to give compound (T-20) (26.1 g; 69percent).Weighing 2.632g choline reagent, 15mLH Weigh 2.632 g of choline reagent (choline reagent), 15 mL of H20, 2 mL of tetrahydrofuran, 8.4 mL of toluene in a 100 mL three-necked flask and heated to 75 ° C. 25.08 g of p-bromobenzyl chloride and 4.4 g of acetaldehyde were dissolved in 12 mL of tetrahydrofuran and slowly added dropwise to the reaction flask. At this temperature for 5 h, TLC showed the reaction to end.The reaction solution was cooled to room temperature, extracted with 50 mL of water and 100 mL of ethyl acetate. The combined wells were dried over anhydrous sodium sulfate and concentrated to dryness. Column chromatography gave 18.24 g of a pale yellow transparent oily liquid compound.yield: 70percentThe reaction was carried out in a 50 cm

Molecular Weight:213.07
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:211.98368
Monoisotopic Mass:211.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:117
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes