Ethanol → Ethyl 2-bromo-6-fluorobenzeneacetate

HRID 1711091Notes

Reaction equation

HRID 1711091 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#N.S(=O)(=O)(O)[OH:13].[CH2:17]([OH:19])[CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([O:19][CH2:17][CH3:18])=[O:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 667177612-(2-Bromo-6-fluorophenyl)acetonitrile

Product 1

HCID 59457717Ethyl 2-bromo-6-fluorobenzeneacetate

Procedure

A solution of 329 (3.89 g, 18.17 mmol) and concentrated sulfuric acid (35 mL) in ethanol (80 mL) was heated to reflux overnight. The mixture was allowed to cool down to room temperature, and poured into a mixture of ice/water, shaken for 15 min, and extracted with AcOEt. The extract was successively washed with water, sat. NaHCO3, water, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford title compound 330 (4.86 g, quantitative yield, contaminated) as a yellow oily liquid. LCMS: 261.0 and 263.0 (M+H)+.

Workup

  1. temperatureto reflux overnight
  2. extractionextracted with AcOEt
  3. washThe extract was successively washed with water, sat. NaHCO3, water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e289b3ed5228489ea64ba622f3d6025b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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