Sulfuric Acid → Methyl 4-bromo-2-methylbenzoate

HRID 2261822Notes

Reaction equation

HRID 2261822 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.OS(O)(=O)=O.[C:17]([O-])([O-])=O.[Na+].[Na+]>CO>[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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-bromo-2-methyl-benzoic acid (1.08 g, 5.02 mmol) in methanol (20 mL) is treated with H2SO4 (0.20 mL). The mixture is stirred at 80° C. for 16 hours and cooled to room temperature. The mixture is neutralized with aqueous Na2CO3 and concentrated, the residue is extracted with ethyl acetate (30 mL×2) and the combined organic layers are dried over sodium sulfate and concentrated to provide 4-bromo-2-methyl-benzoic acid methyl ester (1.25 g, 97%). 1H NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 7.40 (s, 1H), 7.35 (d, 1H), 3.82 (s, 3H), 2.57 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. extractionthe residue is extracted with ethyl acetate (30 mL×2)
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba8f1c2e03e14d4c923cd518608a3c26
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…