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

HRID 532230Notes

Reaction equation

HRID 532230 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-abc1e02898bb415f8dab61d29c9dd72f
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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