Methanol → Methyl 3-bromo-5-nitrobenzoate

HRID 2261894Notes

Reaction equation

HRID 2261894 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].S(Cl)(Cl)=O.[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-nitrobenzoate

Procedure

To a solution of 3-bromo-5-nitrobenzoic acid (1.26 g, 5.12 mmol) in 20 mL MeOH was added thionyl chloride (0.410 mL, 5.63 mmol) dropwise via syringe. The reaction was heated to reflux for 15 h, cooled to rt and concentrated to afford a white solid. 1H NMR (CDCl3) δ 8.77 (m, 1H), 8.53 (m, 1H), 8.47 (m, 1H), 3.98 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 h
  3. concentrationconcentrated
  4. customto afford a white solid

Sources & evidence

ORD record
ord-3568a5f537294f7589160fd317799cf0
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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