Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 1993750Notes

Reaction equation

HRID 1993750 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-ace9fc20e4414d3db851e5793cf73aaf
Source dataset
uspto-grants-2010_01
Patent number
US07652028B2

Reaction notes

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