Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 1642340Notes

Reaction equation

HRID 1642340 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[CH3:17]O>>[Br:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:12][CH3:17])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoate

Procedure

2 mL of concentrated sulfuric acid were added to a solution of 3-bromo-2-methylbenzoic acid (20 g, 93 mmol) in methanol (150 mL). The resultant mixture was refluxed for 6 hours. Methanol was removed under reduced pressure, and the residue was dissolved in a mixture of chloroform (100 mL) and saturated solution of Na2CO3 (100 mL). The organic layer was separated and washed with brine, dried over Na2SO4 and concentrated to provide methyl 3-bromo-2-methylbenzoate (21.1 g). 1H NMR spectrum (in DMSO-d6): δ 7.79 (d, J=8.0 Hz, 1H); 7.69 (d, J=7.9 Hz, 1H); 7.23 (t, 1H); 3.82 (s, 3H).

Workup

  1. customMethanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of chloroform (100 mL) and saturated solution of Na2CO3 (100 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9efe8db802bd4e2881ccf9489938e0ec
Source dataset
uspto-grants-2012_02
Patent number
US08119654B2

Reaction notes

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