Methanol → Methyl 3-bromo-5-nitrobenzoate

HRID 852528

Reaction equation

HRID 852528 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2393363-Bromo-5-nitrobenzoic acid

Product 1

HCID 239341Methyl 3-bromo-5-nitrobenzoateYield 100%

Procedure

To an ice cold solution of 3-bromo-5-nitro-benzoic acid (D5) (2.5 g, 10 mmol, 1 equiv) in MeOH (25 ml) was added SOCl2 (1 ml, 15 mmol, 1.5 equiv) dropwise. The resulting solution was allowed to warm to room temperature and was then stirred at 60° C. for 3 h, cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic layer was washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give 3-bromo-5-nitro-benzoic acid methyl ester (D11) (2.6 g, 100%) as a yellow solid. RT=3.22 min

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic layer was washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f5314e9b09944bcbe504457dea7aaaf
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Linked notes

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