Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 1948663Notes

Reaction equation

HRID 1948663 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13].[CH3:19]O>C1C=CC=CC=1>[Br:8][C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH3:19])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Trimethylsilyldiazomethane solution (2M in Hexane) (60.5 mL, 121 mmol) was added dropwise to a stirred solution of 3-bromo-2-methylbenzoic acid (26 g, 121 mmol) in benzene containing 20% of methanol (total: 300 mL) at rt until solution retained a yellow color. The mixture was concentrated to remove the organic solvent. The remaining oil was poured over a silica gel plug in a 60-mL filter frit funnel and eluting with 500 mL of hexane containing 10% ethyl acetate. The filtrate was then concentrated to dryness to afford the title compound as a bright yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the organic solvent
  3. additionThe remaining oil was poured over a silica gel plug in a 60-mL
  4. filtrationfilter frit funnel
  5. washeluting with 500 mL of hexane containing 10% ethyl acetate
  6. concentrationThe filtrate was then concentrated to dryness

Sources & evidence

ORD record
ord-d340ef4cab004fc1bfc1970f5e30f4a3
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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