Thionyl Chloride → 1-(1-Chloroethyl)-2-fluorobenzene

HRID 1833851Notes

Reaction equation

HRID 1833851 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12](O)[CH3:13]>C(Cl)(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([Cl:3])[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1230662-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 135643251-(1-Chloroethyl)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (100 ml.) was added to a solution of 1-(2-fluorophenyl)ethanol [described by McCall, J.A.C.S. 74, 4809 (1952)] (105 g.) in dry chloroform (200 ml.). After the vigorous initial reaction had subsided, the solution was heated at reflux on a steam bath for 30 minutes. The excess of thionyl chloride was removed by repeated co-distillation with dry toluene and the residue was diluted with diethyl ether, washed with water (2 × 100 ml.), dried over sodium sulphate, filtered and evaporated to a yellow liquid, which was distilled to give 1-(2-fluorophenyl)ethyl chloride (73.2 g.), b.p. 70°-75° C./20 mm.Hg, as a pale yellow oil.

Workup

  1. customAfter the vigorous initial reaction
  2. temperaturethe solution was heated
  3. temperatureat reflux on a steam bath for 30 minutes
  4. customThe excess of thionyl chloride was removed
  5. additionthe residue was diluted with diethyl ether
  6. washwashed with water (2 × 100 ml.)
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to a yellow liquid, which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-97e5ae75f6dc4ff9b4ec9afd062596c0
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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