Methanol → Methyl 2-Bromo-4-nitrobenzoate

HRID 496630Notes

Reaction equation

HRID 496630 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]O>>[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 3135342-Bromo-4-nitrobenzoic acid

Product 1

HCID 15833211Methyl 2-Bromo-4-nitrobenzoate

Procedure

Compound 26 in methanol was treated with SO2Cl2 and the resulting solution heated at reflux for18 h. The reaction mixture was then evaporated, pre-absorbed on silica (Merck, 9385) and purified by chromatography, eluting with 10% ethyl acetate/i-hexane. Appropriate fractions were combined and evaporated to give methyl 2-bromo-4-nitro-benzoate (compound 27).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for18 h
  3. customThe reaction mixture was then evaporated
  4. custompre-absorbed on silica (Merck, 9385)
  5. custompurified by chromatography
  6. washeluting with 10% ethyl acetate/i-hexane
  7. customevaporated

Sources & evidence

ORD record
ord-dff9c183e7ac4755bae7a188497d9847
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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