Phosphorus oxide (P4O10) → 3-Bromo-5-methylbenzonitrile

Participants

Reaction Steps

To a suspension of 3-bromo-5-methylbenzamide (15.0 g, 70.1 mmol) in CHCl3 was added phosphorous pentoxide (29.8 g, 210.2 mmol) and the mixture was kept refluxing for 2 days (monitored by TLC). The reaction was allowed to cool to room temperature, and put into the ice water under the condition of stirring. The organic layer was separated and the aqueous layer was extracted with dichloromethane (150 mL×2). The combined extracts were washed with brine, dried over NaSO4. The product, 3-bromo-5-methylbenzonitrile (7.20 g, 52%), was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): δ 7.60-7.56 (m, 2 H), 7.40-7.39 (m, 1 H), 2.39 (s, 3 H).

Provenance & Evidence