Methanol → Methyl 4-bromo-2-fluoro-5-methylbenzoate

HRID 508188Notes

Reaction equation

HRID 508188 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.O=S(Cl)Cl.[CH3:17]O>>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 341745874-Bromo-2-fluoro-5-methylbenzoic acid

Product 1

HCID 66817979Methyl 4-bromo-2-fluoro-5-methylbenzoate

Conditions

Temperature
80 °C

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).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. washThe resulting crude solid was washed with PE

Sources & evidence

ORD record
ord-41752e8eda6a478d996396309c9f08f6
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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