Methanol → Methyl 2-(2-fluoro-5-nitrophenyl)acetate

HRID 64347Notes

Reaction equation

HRID 64347 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13].OS(O)(=O)=O.O.[CH3:21]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH3:21])=[O:13]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 8493592-Fluoro-5-nitrophenylacetic acid

Product 1

HCID 67451325Methyl 2-(2-fluoro-5-nitrophenyl)acetateYield 93.4%

Procedure

To a solution of 2-(2-fluoro-5-nitrophenyl)acetic acid (1.0 g, 5.0 mmol) in CH3OH (20 mL) was added con. H2SO4 (0.50 mL), the reaction was warmed to 80° C. and stirred for about 3 hr. After cooling down to RT, the reaction was poured into water (20 mL) and concentrated to remove CH3OH. The aqueous was extracted with ethyl acetate (2×20 mL), the combined organic phases were washed brine (10 mL), dried over Na2SO4, filtered and concentrated to afford the product about 1.0 g (93.4%) as a colorless oil. MS (ESI) m/e [M+1]+ 214.0.

Workup

  1. concentrationconcentrated
  2. customto remove CH3OH
  3. extractionThe aqueous was extracted with ethyl acetate (2×20 mL)
  4. washthe combined organic phases were washed brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7da12f1217f848d7ad182a8134de8510
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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