Dimethylformamide → HCID 18006169, compound

Participants

Reaction Steps

A 250 mL round bottom flask was charged with the 4-Bromo-3-(dibromomethyl)benzoic acid prepared as described above (114.6 g, 307 mmol) in anhydrous toluene (1.14 L) and anhydrous DMF (6.3 mL). The resulting suspension was stirred at RT under an argon atmosphere. Oxalyl chloride (29.5 mL, 338 mmol) was added dropwise. The reaction mixture became a clear yellow solution at the end of the reaction. HPLC indicated the reaction was complete in 2 hours. The solution was decanted away from a gummy oil deposited at the bottom of the reaction flask and the solution was concentrated on a rotary evaporator and then on a high vacuum pump overnight to dryness. The 4-Bromo-3-(dibromomethyl)benzoyl chloride was obtained as a light brown solid 115.02 g, 95.7% yield and area percent=93.5%. The 1H NMR spectrum was consistent with the assigned structure.

Provenance & Evidence