2-CHLORO-3-NITROBENZALDEHYDE

8.43 g (39.09 mmol) of pyridinium chlorochromate (PCC) were added to a solution of 6.11 g (32.57 mmol) of (2-chloro-3-nitrophenyl)methanol in 120 ml of dichloromethane, and the mixture was stirred at room temperature for 12 hours. After complete conversion, the solvent was evaporated to dryness under reduced pressure. The residue obtained was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 20:1). This gave 4.82 g (25.97 mmol, 79.7percent of theory) of the title compound.GC-MS (method 3): RA solution of oxalyl chloride in dichloromethane (2.0M, 116 mmol) was chilled to -70° C. (internal temperature) under a nitrogen atmosphere. DMSO (15 mL, 211.3 mmol) was added dropwise maintaining Step 2. 2-Chloro-3-nitrobenzaldehyde; A 250-mL 3-necked round-bottom flask was charged with a solution of oxalyl chloride (5.42 g, 42.70 mmol, 1.10 equiv) in DCM (100 mL). To this was added a solution of DMSO (6.65 g, 85.11 mmol, 2.20 equiv) in DCM (15 mL) drop wise -78° C. 2-Chloro-3-nitrophenyl)methanol (7.23 g, 38.54 mmol, 1.00 equiv) in DCM (35 mL) was added into the solution at -78° C. and allowed to stir for 1 hour. Then, TEA (30 mL) was added at this temperature and allowed to stir for an additional hour. Upon completion, the reaction was quenched with water and extracted with DCM (3.x.100 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with PE:EA (10:1) affording 2-chloro-3-nitrobenzaldehyde as light yellow solid (5.3 g, 74percent).

Molecular Weight:185.56
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:184.9879707
Monoisotopic Mass:184.9879707
Topological Polar Surface Area:62.9
Heavy Atom Count:12
Complexity:192
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes