Methyl 4-bromo-3-methylbenzoate → 4-Bromo-3-methylbenzoic acid

HRID 1514869Notes

Reaction equation

HRID 1514869 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[CH:5]=1>[OH-].[Na+].C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:12])=[O:2])=[CH:5][C:6]=1[CH3:11]

Participants

4

Reactant 1

HCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 821314-Bromo-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl-4-bromo-3-methylbenzoate (400 mg) in 2N NaOH aqueous solution (3 mL) and THF (5 mL) was stirred at room temperature for 16 h. The mixture was washed with Et2O. The aqueous layer was acidified with 4N HCl aqueous solution, extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give 4-bromo-3-methyl-benzoic acid as white powder: MS (m/z) 215 (M+1); 1H NMR (CD3OD, 400 MHz) δ 7.95 (s, 1H), 7.76 (d, 1H), 7.64 (d, 1H), 2.47 (s, 3H).

Workup

  1. washThe mixture was washed with Et2O
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83378f179d1b46ed9ece2cd97ba943f3
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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