Methanol → Methyl 4-fluoro-3-nitrobenzoate

HRID 1520131Notes

Reaction equation

HRID 1520131 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[CH3:18]O>>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:18])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoateYield 93%

Procedure

Thionyl chloride (191.4 g, 1.61 mol) was added to a solution of 4-fluoro-3-nitrobenzoic acid (150.0 g, 810.81 mmol) in methanol (500 ml) at 0° C. The resulting solution was heated to reflux overnight, concentrated in vacuo, the product was precipitated by the addition of petroleum ether (200 ml), and the solids were collected by filtration to afford methyl 4-fluoro-3-nitrobenzoate as a light yellow solid (150 g, 93%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. customthe product was precipitated by the addition of petroleum ether (200 ml)
  5. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-9e6a331db11b43a19581227aae2a357f
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…