Methanol → Methyl 4-Bromo-2-chlorobenzoate

HRID 878697Notes

Reaction equation

HRID 878697 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.O=S(Cl)Cl.[CH3:16]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoateYield 85%

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-bromo-2-chlorobenzoic acid (6.11 g, 25.94 mmol) in methanol (60 mL) cooled to 0° C. was added SOCl2 (6.17 g, 51.89 mmol) drop wise. The reaction mixture was stirred at 0° C. for 15 min then at 70° C. for 3 h. It was then cooled to room temperature and removed the solvent. The residue was purified by flash column chromatograph to give 5.52 g of the title compound (85%). 1H NMR (400 MHz, CDCl3): δ 3.92 (3H, s), 7.45 (1H, dd, J=2.0 Hz, 8.4 Hz), 7.63 (1H, d, J=2.0 Hz), 7.71 (1H, d, J=8.4 Hz).

Workup

  1. waitat 70° C. for 3 h
  2. temperatureIt was then cooled to room temperature
  3. customremoved the solvent
  4. customThe residue was purified by flash column chromatograph

Sources & evidence

ORD record
ord-3a4f29f6127f4e4d86d269c98f90a4da
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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