Yield:45767-66-6 88%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane; for 3 h;Heating / reflux;

Steps:

12

A mixture of 77.6 g (0.54 mol) of 2-chloro-4-fluorotoluene, 95.6 g(0.54 mol) of N-bromosuccinimide, 1 g of benzoyl peroxide, and 1000 ml of carbon tetrachloride were refluxed for 3 h. The resulting mixture was cooled to room temperature and then filtered through a glass frit (G3). The precipitate was additionally washed with 3 x 100 ml of carbon tetrachloride. The combined filtrate was evaporated to dryness. Fractional distillation of the residue gave pure title product, bp 97-99°C/10 mm Hg. Yield 106 g (88%).Anal. calc. for C₇H₅BrClF: C, 37.62 H, 2.26 Found: C, 37.79; H, 2.34.¹H NMR (CDCl₃): δ 7.41 (dd, J=8.4 Hz, J=6.0 Hz, IH, 6-H), 7.13 (dd, J=8.4 Hz, J=2.6 Hz, IH, 3-H), 6.97 (dt, J=8.4 Hz, J=2.6 Hz, IH, 5-H), 4.55 (s, 2H, CH₂).

References:

WO2007/70041,2007,A1 Location in patent:Page/Page column 115