Methanol → Methyl 4-fluoro-5-methyl-2-nitrobenzoate

HRID 1750850Notes

Reaction equation

HRID 1750850 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.O=S(Cl)Cl.[CH3:19]O>>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 581158484-Fluoro-5-methyl-2-nitrobenzoic acid

Product 1

HCID 58115689Methyl 4-fluoro-5-methyl-2-nitrobenzoate

Procedure

To a solution of the crude 4-fluoro-5-methyl-2-nitrobenzoic acid (5 g) in MeOH (50 mL) was slowly added SOCl2 (3.5 mL, 48 mmol) dropwise and the resulting mixture was refluxed overnight. Then the solvent was removed to give crude methyl 4-fluoro-5-methyl-2-nitrobenzoate (5 g) as a white solid. It was used in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customThen the solvent was removed

Sources & evidence

ORD record
ord-6734a375690f4bd4ae54f74fe4dec284
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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