Methanol → Methyl 3-bromo-5-nitrobenzoate

HRID 852527

Reaction equation

HRID 852527 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 94%

Procedure

To a solution of 3-bromo-5-nitro-benzoic acid (D5) (22.3 g, 90.6 mmol, 1 equiv) in MeOH (300 ml) at 0° C. was added SOCl2 (7.9 ml, 108 mmol, 1.2 equiv) dropwise. The resulting solution was stirred at reflux for 4 hours then cooled to room temperature and concentrated in vacuo. The residue was diluted with AcOEt, washed twice with 2N aqueous NaOH solution and once with brine, dried over MgSO4 and concentrated in vacuo to give 3-bromo-5-nitro-benzoic acid methyl ester (D11) (22.1 g, 94%) as a pale brown solid. RT=3.18 min

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with AcOEt
  4. washwashed twice with 2N aqueous NaOH solution and once with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af069a73802042128b68719f111f09ae
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Linked notes

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