Hydrochloric Acid → Methyl 4-bromo-2-methylbenzoate

HRID 2171093Notes

Reaction equation

HRID 2171093 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.Cl.[CH3:13]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 4-bromo-2-methylbenzoic acid (3 g) in methanol (70 mL) was added concentrated hydrochloric acid (5 mL) and the reaction mixture was heated to 60° C. for 16 h. The reaction mixture was concentrated under reduced pressure, the residue was basified with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford Methyl 4-bromo-2-methylbenzoate as a solid (2 g, 62%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined dichloromethane layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2de2810c97304755a5406714a2308167
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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