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477199-77-2

4-(Bromomethyl)-2-fluorobenzoicacid synthesis

6synthesis methods
-

Yield:477199-77-2 62%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 90; for 3 h;

Steps:

13.1

[00202] Step 1 : AIBN (533 mg, 3.24 mmol) and N-bromosuccinimide (6.35 g, 35.68 mmol) were added to 2-fluoro-4-methyl-benzoic acid (5.0 g, 32.4 mmol) in CC14 (50 mL) and the reaction mixture heated for 3 h at 90 °C. The reaction mixture was cooled, filtered, and the filter cake was washed once with CC14, then three times with water. The filter cake was then dissolved in a 1 : 1 mixture of acetonitrile/MeOH, dried over a2S04, filtered and concentrated in vacuo to afford 4-(bromomethyl)-2-fluoro-benzoic acid (4.7 g, 62% yield) as an off-white solid. ? NMR (400 MHz, DMSO-i?) 513.30 (s, 1H), 7.89 - 7.81 (m, 1H), 7.42 (dd, J = 8.9, 4.0 Hz, 1H), 7.38 (dd, J = 8.0, 1.5 Hz, 1H), 4.73 (s, 2H).

References:

WO2011/143426,2011,A1 Location in patent:Page/Page column 71