Reaction #63589

Reaction equation

α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetyl chloride

ethanol

→

ethyl α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetate

Solvents

methylbenzene

Conditions

Workup

1. 1
   OtherThe reaction mixture was evaporated
2. 2
   Otherthe latter was evaporated again
3. 3
   WashThe whole was washed with a saturate sodium hydrogen carbonate solution and with water
4. 4
   Otherdried
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by column-chromatography over silica gel using
8. 8
   workup.ADDITIONa mixture of trichloromethane and hexane (50:50 by volume) as eluent
9. 9
   OtherThe pure fractions were collected
10. 10
    Otherthe eluent was evaporated

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).

Source