Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 896016Notes

Reaction equation

HRID 896016 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Procedure

A mixture of 4-bromo-2-methylbenzoic acid (20 grams, 215 mmol), methanol (500 mL) and concentrated sulfuric acid (1 mL) was refluxed for 8 hours. The mixture was concentrated in vacuo, diluted with ether, washed twice with water, and the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo, affording 17 grams of 4-bromo-2-methylbenzoic acid methyl ester. 1H NMR (CDCl3, 500 MHz): δ 7.77 (d, 1H, J=8.3 Hz), 7.41 (s, 1H), 7.37 (d, 1H, J=8.3 Hz), 3.89 (s, 3H), 2.58 (s, 3H) ppm.

Workup

  1. temperaturewas refluxed for 8 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with ether
  4. washwashed twice with water
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d8e51b7fea64479b72f95faff7e79ca
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

Loading…