5-BROMO-2-IODOBENZALDEHYDE

To a stirred solution of PDC (11.0 g, 0.0288 mol) in CHA solution of oxalyl chloride (1 .99 mL, 23.04 mmol, 1 .6 equiv) in DCM (25 mL) was cooled to -70°C and DMSO (2.44 mL, 34.5 mmol, 2.4 equiv) in DCM (25 mL) was added at -65°C to -70°C. The reaction mixture stirred for 10 minutes under nitrogen atmosphere at - 70°C and then (5-bromo-2-iodophenyl)methanol (4.55 g, 14.4 mmol, 1 .0 equiv) in DCM (100 mL) was added. The reaction mixture was stirred at -65°C for 15 minutes and triethylamine (10 mL, 72 mmol, 5.0 equiv) was added. The reaction mixture was allowed to warm to -10°C and stir for 1 h. Water (40 mL) was added and the reaction mixture was allowed to warm to room temperature. The organic layer was separated and evaporated to obtain 5-bromo-2-iodobenzaldehyde (4.2 g, 93 percent) as white solid. 5-bromo-2-iodobenzaldehyde (17a). A solution of N-methyl morpholine-N- oxide (870 mg, 7.2 mmol) and 4 A sieves (5.8 g) in acetonitrile (18 mL) in a dried250 mL Schlenk flask under nitrogen was cooled to 0 °C, and benzyl bromide 15a0(880 mg, 2.3 mmol) was added at once. The reaction mixture was held at 0 °C for 2 h before warming to room temperature. The reaction mixture was then filtered through a short plug (Si03.11 g (10 mmol) of

Molecular Weight:310.91
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:309.84902
Monoisotopic Mass:309.84902
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes