Ethanol → (3-Bromo-2-fluoro-phenyl)-acetic acid ethyl ester

HRID 1466959Notes

Reaction equation

HRID 1466959 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH2:8][C:9]#N)[CH:5]=[CH:6][CH:7]=1.[OH:12]S(O)(=O)=O.[CH3:17][CH2:18][OH:19]>>[CH2:18]([O:19][C:9](=[O:12])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[F:11])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 26985257(3-Bromo-2-fluorophenyl)acetonitrile

Product 1

HCID 66765390(3-Bromo-2-fluoro-phenyl)-acetic acid ethyl ester

Procedure

To a stirred solution of 3-bromo-2-fluorophenylacetonitrile (2.5 g, 11.7 mmol) in absolute EtOH (25 mL) at room temperature was added concentrated H2SO4 (4 mL) and the mixture was warmed to reflux. After 48 hrs, the reaction was cooled to room temperature, evaporated under reduced pressure, diluted with EtOAc (100 mL) and partitioned with saturated aqueous sodium bicarbonate (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness to afford the title compound.

Workup

  1. temperaturethe mixture was warmed to reflux
  2. customevaporated under reduced pressure
  3. additiondiluted with EtOAc (100 mL)
  4. custompartitioned with saturated aqueous sodium bicarbonate (50 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32877a61806143859e31a48aa492f177
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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