4-Bromo-2-methylbenzoic acid → Methyl 4-bromo-2-methylbenzoate

HRID 906149Notes

Reaction equation

HRID 906149 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.[CH3:12][Si](C=[N+]=[N-])(C)C>O1CCCC1.CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 995704-Bromo-2-methylbenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4-bromo-2-methylbenzoic acid (15.1 g, 0.070 mol) in tetrahydrofuran (180 mL) and methanol (45 mL) was slowly added (trimethylsilyl)diazomethane (2.0M in hexanes, 42 mL, 0.084 mol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, at which time it was concentrated in vacuo to afford methyl 4-bromo-2-methylbenzoate (16 g, 100%) as a yellow oil. The residue was taken to the next step without further purification. 1H NMR (400 MHz, CDCl3): 7.78 (d, 1H), 7.42 (s, 1H), 7.38 (d, 1H), 3.88 (s, 3H), 2.58 (s, 3H). MS (EI) for C9H9BrO2: 230 (MH+).

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-0961fb90351045bc8bd6ffece0d1b1ff
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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