Ammonium Chloride → 2-(4-Chloro-2-fluorobenzoyl)cyclopropanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

5.67 g (134 mmol) of lithium chloride and 0.7 ml of a 0.1N solution of diisobutylaluminum hydride in THF were added to 6.50 g (268 mmol) of magnesium turnings in 30 ml of THF. The mixture was stirred for five minutes and cooled to 0° C., 22.4 g (107 mmol) of 1-bromo-4-chloro-2-fluorobenzene were added, and the mixture was allowed to warm to RT and was stirred at RT overnight. The reaction solution was added dropwise under argon to a solution of 15.0 g (97.3 mmol) of the compound from Example 73A in 10 ml of THF, and the reaction mixture was heated under reflux for 2 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and extracted with dichloromethane, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 95/5) to result in 5.40 g (25% of theory) of the title compound.

Provenance & Evidence