METHYL 2-BROMOMETHYL-4-FLUORO-BENZOATE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-bromomethyl-4-fluoro-benzoic acid methyl ester (17 g, 68.8 mmol) in THF (200 mL) was added PMBNH2 (23.6 g, 172 mmol) at 0° C. After stirring at room temperature for 16 hours, the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromatography to give the title compound (13 g, yield 69%) as a solid. the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-bromomethyl-4-fluoro-benzoic acid methyl ester (17 g, 68.8 mmol) in THF (200 mL) was added PMBNH2 (23.6 g, 172 mmol) at 0° C. After stirring at room temperature for 16 hours, the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromatography to give the title compound (13 g, yield 69%) as a solid. the reaction mixture was concentrated in vacuo to give a crude product which was then purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-fluoro-2-methyl-benzoic acid methyl ester (12.7 g, 75.5 mmol), NBS (13.4 g, 75.5 mmol), and di-benzoyl peroxide (BPO) (0.85 g, 3.5 mmol) in CCl4 (200 mL) was heated to reflux for 3 hours until all starting material was consumed. After vacuum filtration, the filtrate concentrated in vacuo to give a crude product (17 g, yield 91%), which was used in the next step reaction without further purification. was heated to reflux for 3 hours until all starting material was consumed After vacuum filtration the filtrate concentrated in vacuo