2-Bromo-4,5-difluorobenzaldehyde

A solution of (2-bromo-4, 5-difluoro-phenyl)-methanol (1.23 g, 5.50 mmol), triethylamine (1.39 g, 13.75 mmol) and dimethyl sulfoxide (1.72 g, 22.00 mmol) in dichloromethane (25 ml_) was cooled to 0 °C. Then, sulfur trioxide-pyridine (1.32 g, 8.25 mmol) was added portionwise. After one hour stirring at 0 °C, a second batch of triethylamine (1.39 g, 13.75 mmol), dimethyl sulfoxide (1.72 g, 22.00 mmol) and sulfur trioxide-pyridine (1.32 g, 8.25 mmol) were added to the above reaction mixture. After another 30 minutes at 0 °C, the reaction solution was diluted with dichloromethane (50 ml_), and then washed with saturated sodium bicarbonate and saturated sodium thiosulfate. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSepA mixture of Pd(PPh3)4 (260 mg, 0.23 mmol), Cul (43 mg, 0.23 mmol), 2-bromo-4, 5- difluorobenzaldehyde (1 .00 g, 4.50 mmol) and ethynyl trimethylsilane (1 .55 g, 15.80 mmol) in TEA (10 mL) was stirred at 70 C overnight. The mixture was concentrated to dryness. EtOAc (20 mL) was added and the mixture was filtered through a pad of Celite. The mixture was concentrated to dryness and the residue was purified by column chromatography (gradient 5-30% EtOAc in PE) to give the title compound as a yellow oil.A mixture of Pd(PPh3)4 (260 mg, 0.23 mmol), Cul (43 mg, 0.23 mmol), 2-bromo-4, 5- difluorobenzaldehyde (1 .00 g, 4.50 mmol) and ethynyl trimethylsilane (1 .55 g, 15.80 mmol) in TEA (10 mL) was stirred at 70 C overnight. The mixture was concentrated to dryness. EtOAc (20 mL) was added and the mixture was filtered through a pad of Celite. The mixture was concentrated to dryness and the residue was purified by column chromatography (gradient 5-30% EtOAc in PE) to give the title compound as a yellow oil.

Molecular Weight:221.00
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:219.93353
Monoisotopic Mass:219.93353
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes