Ethanol → HCID 19883448, compound

HRID 35311Notes

Reaction equation

HRID 35311 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6](Cl)=[O:7].[CH2:23]([OH:25])[CH3:24]>CC1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6]([O:25][CH2:23][CH3:24])=[O:7]

Participants

4

Reactant 2

HCID 702EthanolHCID 19883439a-(3-Bromopropyl)-4-fluoro-alpha-(4-fluorophenyl)benzeneacetyl chloride

Product 1

HCID 19883448HCID 19883448, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 30 parts of α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetyl chloride, 9.3 parts of ethanol and 90 parts of methylbenzene was stirred overnight at room temperature. The reaction mixture was evaporated, the residue was taken up in ethanol and the latter was evaporated again. The residue was taken up in 2,2'-oxybispropane. The whole was washed with a saturate sodium hydrogen carbonate solution and with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and hexane (50:50 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 19.6 parts of ethyl α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetate as a residue (intermediate 18).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe latter was evaporated again
  3. washThe whole was washed with a saturate sodium hydrogen carbonate solution and with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and hexane (50:50 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-c51f10526b494af2af34f33182198b3a
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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