Methanol → Methyl 3-bromo-4-chlorobenzoate

HRID 877607Notes

Reaction equation

HRID 877607 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355443-Bromo-4-chlorobenzoic acid

Product 1

HCID 22352523Methyl 3-bromo-4-chlorobenzoate

Procedure

3-Bromo-4-chlorobenzoic acid (200 mg, 0.849 mmol) was refluxed in the presence of concentrated sulfuric acid (5.49 mg, 0.042 mmol) in methanol (10 mL) at 70° C. for overnight. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum, and the compound was purified by column chromatography affording the title compound (130 mg). 1H NMR (400 MHz, CDCl3): δ 8.29 (d, 1H, J=2.0 Hz), 7.91 (dd, 1H, J=2.0 & 8.4 Hz), 7.52 (d, 1H, J=8.4 Hz), 3.92 (s, 3H). ESI-MS: 250.9 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum
  3. customthe compound was purified by column chromatography

Sources & evidence

ORD record
ord-2e4bfab63239421e8f63696912520f30
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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