methyl 4-bromo-2-(bromomethyl)-5-fluorobenzoate

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

Procedure: This compound was prepared using procedures analogous to those described for the synthesis of Example 52, Step 6 starting from methyl 4-bromo-2-(bromomethyl)-5-fluorobenzoate and isopropylamine. LC/MS: (M+H)+=271.9/273.9. This compound was prepared

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

Procedure: A mixture of methyl 4-bromo-5-fluoro-2-methylbenzoate (1.0 g, 4.0 mmol) (Ellanoval Laboratories Cat. No. 38-0304), N-bromosuccinimide (900. mg, 5.06 mmol) and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (50 mL) was refluxed under a nitrogen atmosphere for 4 h. After cooling the mixture was diluted with methylene chloride. The organic solution was washed with brine, then dried over Na2SO4. After filtration the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (1.2 g). After cooling the mixture The organic solution was washed with brine dried over Na2SO4 After filtration the filtrate was concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)