Benzene → 4-Bromo-2-methyl-benzoic acid isopropyl ester

HRID 2377438Notes

Reaction equation

HRID 2377438 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.O.[CH:18]1[CH:23]=CC=C[CH:19]=1>C(O)(C)C>[CH:18]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11])([CH3:23])[CH3:19]

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 225688974-Bromo-2-methyl-benzoic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-bromo-2-methyl-benzoic acid (Aldrich, 5.4 g, 25 mmol) in benzene (75 mL) and isopropanol (75 mL) was treated with concentrated sulfuric acid (1.5 mL) and heated to reflux over 4 days using a Dean-Stark water trap. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The organic phase was washed with water and saturated, aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a clear oil that was used as such for the next step (6.12 g, 95%).

Workup

  1. temperatureheated
  2. temperatureto reflux over 4 days
  3. customThe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with diethyl ether
  6. washThe organic phase was washed with water
  7. dry with materialsaturated, aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a4337873e01445a9a943529f70d2a8f9
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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