2-Fluorobenzyl bromide

Method 1,
Mix 2-fluorotoluene, N-bromosuccinimide, benzoyl peroxide, and chloroform. Purge with argon gas, maintaining a pressure of 2 atmospheres and a temperature of 100°C. Stir for 1.5 hours to obtain a mixture containing 2-fluorobenzyl bromide.
Method 2,

At 0°C, add CBr4 (31.6 g, 95.2 mmol) in small batches to a DCM solution of (2-fluorophenyl)methanol (Aldrich, 10.0 g, 79.3 mmol) and triphenylphosphine (29.1 g, 111 mmol). Stir the mixture at room temperature for 2 hours.

The solvent was evaporated, and the residue was purified by rapid chromatography (cyclohexane:ethyl acetate 95:5) to give 2-fluorobenzyl bromide (14 g, 93%).

clear colorless to slightly yellow liquid

2-Fluorobenzyl bromide was used:

• in the synthesis of 2-pyrrolo[2,3-d]pyrimidines
• as alkylating agent during the synthesis of 8-alkylated imidazolo[1,2-a]pyrimid-5-ones
• in the synthesis of prasugrel