Reaction #595370

Reaction equation

4-bromo-2-fluoro-5-methylbenzoic acid

SOCl2

CH3OH

→

title compound

methyl 4-bromo-2-fluoro-5-methylbenzoate

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   workup.ADDITIONthe residue was diluted with EtOAc
3. 3
   Washwashed with H2O, brine
4. 4
   Dryingdried over anhydrous Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   WashThe resulting crude solid was washed with PE

Procedure

To a solution of 4-bromo-2-fluoro-5-methylbenzoic acid (i-2a) (1.87 g, 8 mmol) in CH3OH (50 mL) at 0° C. was added SOCl2 (6 mL, 80 mmol) dropwise. Then the mixture was heated to 80° C. for 2 h. The solvent was removed in vacuo and the residue was diluted with EtOAc and washed with H2O, brine, dried over anhydrous Na2SO4, and concentrated. The resulting crude solid was washed with PE to give the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, d), 7.37 (1H, d), 3.92 (3H, s), 2.39 (3H, s).

Source