Hydrochloric Acid → 3-Trifluoroacetylfuran

HRID 2800

Reaction equation

HRID 2800 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15].Cl>C(OCC)C>[F:12][C:13]([F:20])([F:19])[C:14]([C:2]1[CH:6]=[CH:5][O:4][CH:3]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 891643-BromofuranHCID 178418339Butyllithium

Product 1

HCID 189363153-Trifluoroacetylfuran

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Bromofuran (20 g) was added to a solution of n-butyllithium (2.5M in hexanes, 60 ml) in diethyl ether (200 ml) at -70° C. After 30 minutes, ethyl trifluoroacetate (28.6 g) was added slowly. After a further 1 hour the mixture was allowed to warm to room temperature and was then left to stir overnight. 1M Hydrochloric acid (100 ml) was added and the mixture stirred for 5 minutes. The organic layer was separated, washed, dried and evaporated. The residue was distilled to give the title compound. B.p. 118° C.

Workup

  1. waitAfter a further 1 hour the mixture was allowed
  2. waitwas then left
  3. stirringthe mixture stirred for 5 minutes
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-ca2c656728094237986dc15e1b9e16c6
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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