3-Iodobenzaldehyde

Pale yellow crystalline powder

General procedure: The general method for ultrasonically assisted brominationreaction is almost similar to conventional reaction as mentionedabove. A centimolar (0.01 mol) organic substrate (phenols, anilines, or acetanilides), 0.001 mol potassium halide(KBr), about 50 mg of dilute KHSO4, and hypervalent Cr(VI) reagent (IQCC or IQDC) were suspended in about30 mL solvent (DCE or ACN) in a previously cleaned roundbottom(R.B) flask placed in a sonicator. The reaction mixtureis sonicated at room temperature about 30–40 min. Progressof the reaction was monitored by TLC technique. Workupprocedure after completion of the reaction mixture is similarto the one described previously.General procedure: To a suspension of 1-(chloromethyl)-4-fluoro-1, 4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (1, 0.975 mmol) in MeCN(3 mL) the amine (2, 0.75 mmol) dissolved in MeCN (3 mL) was added dropwise at r.t. The reaction was stirred at r.t. for another20 min. The solvent was evaporated, and the obtained residuewas purified via flash column chromatography using silica gel as stationary phase.General procedure: To a suspension of 1-(chloromethyl)-4-fluoro-1, 4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (1, 0.975 mmol) in MeCN(3 mL) the amine (2, 0.75 mmol) dissolved in MeCN (3 mL) was added dropwise at r.t. The reaction was stirred at r.t. for another20 min. The solvent was evaporated, and the obtained residuewas purified via flash column chromatography using silica gel as stationary phase.3-Iodobenzaldehyde (12) A suspension of pyridinium chlorochromate (2.45 g, 11.4 mmol) and dry celite (-2. 00 g) in dry dichloromethane (20 ml) was stirred at room temperature for 15 min. 3-Iodobenzyl alcohol (11) (1.02 g, 4.35 mmol) in dry dichloromethane (5 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 paste which was re-dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. This gave a clear, colourless solution which was concentrated to give 3-iodobenzaldehyde (12) as a white solid (0.953 g, 95percent). 1H nmr (400 Mz, CDC13) : 67. 29 (t, J 7. 8 Hz, 1H) H5; 7.85 (brd, J 7. 8 Hz, 1H) H6; 7.96 (brd, J7. 8 Hz, 1H) H4; 8.21 (brs, 1H) H2; 9.93 (s, 1H) CHO.A solution of 3-iodobenzyl alcohol (Aldrich, 4.72g, 20 mmol) in dichloromethane (50mL) and acetonitrile (5mL) was treated sequentially with 4 A molecular sieves powder (5g), tetra-n-propyl ammoniumperruthenate (0. 1 g) and N-methyl morpholine-N-oxide (2.34g, 40mmol). After stirring at ambient temperature for 3h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10percent ethyl acetate in hexane as the eluent to afford the title compound (3.7g, 80percent). It was used as such for the next step.3-Iodo-benzaldehyde; A solution of 3-iodobenzyl alcohol (Aldrich, 4.72g, 20 mmol) in dichloromethane (50mL) and acetonitrile (5mL) was treated sequentially with 4 A molecular sieves powder (5g), tetra-n-propyl ammoniumperruthenate (0. lg) and N- methyl morpholine-N-oxide (2.34g, 40mmol). After stirring at ambient temperature for 3h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10percent ethyl acetate in hexane as the eluent to afford the title compound (3.7g, 80percent). It was used as such for the next stepGeneral procedure: In a 25 mL round-bottomed flask equipped with a reflux condenser, a mixture of 1 g PWM/SiO

Molecular Weight:232.02
XLogP3:2.2
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