Methanol → Methyl 2-(4-fluoro-3-nitrophenyl)acetate

HRID 48169Notes

Reaction equation

HRID 48169 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].S(=O)(=O)(O)O.[CH3:20]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:20])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 111272614-Fluoro-3-nitrophenylacetic acid

Product 1

HCID 22742120Methyl 2-(4-fluoro-3-nitrophenyl)acetate

Procedure

4-Fluoro-3-nitrophenylacetic acid (31.0 g, 0.156 mol) was added to a mixture of concentrated sulfuric acid (1.6 ml) and methanol (160 ml) and the mixture was stirred for 3 days at room temperature. Most of the solvent was removed in vacuo and the residue was partitioned between diethyl ether and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo to give methyl 4-fluoro-3-nitrophenylacetate (27.2 g) as a yellow oil.

Workup

  1. customMost of the solvent was removed in vacuo
  2. customthe residue was partitioned between diethyl ether and water
  3. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-cda7c95d3a9d45f4a7273c50490ba941
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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