Methanol → Methyl 3-bromo-5-nitrobenzoate

HRID 541736

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(=O)(=O)(O)O.[CH3:19]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 2393363-Bromo-5-nitrobenzoic acid

Product 1

HCID 239341Methyl 3-bromo-5-nitrobenzoateYield 95%

Conditions

Temperature: 0 °C

Procedure

A solution of 3-bromo-5-nitrobenzoic acid (15.4 g, 62.6 mmol) in methanol (120 mL) and sulfuric acid (1.7 mL, 31 mmol) was heated to reflux overnight. After cooling to 0° C. for 0.5 h, the precipitated solid was filtered to give the desired product as a white solid (15.5 g, 95%). LCMS for C8H7BrNO4 (M+H)+: m/z=260.0, 262.0.

Workup

temperatureto reflux overnight
filtrationthe precipitated solid was filtered

Sources & evidence

ORD record: ord-2847e7bb46cf4f01b532d26082e37923
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Linked notes

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