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

HRID 80624Notes

Reaction equation

HRID 80624 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>[Cl:3][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[F:5])[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1230662-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 135643251-(1-Chloroethyl)-2-fluorobenzeneYield 76.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

767 mg of thionyl chloride are added to a solution of 1 g of commercial 1-(2-fluorophenyl)ethanol in 20 ml of chloroform. After stirring overnight at a temperature in the region of 20° C., the reaction mixture is washed with a saturated aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure. 780 mg of 1-(1-chloroethyl)-2-fluorobenzene are thus obtained, said product being used as it is in the next stage.

Workup

  1. washthe reaction mixture is washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f35e386606384ea29d7824fbfb6bb309
Source dataset
uspto-grants-2014_09
Patent number
US08846670B2

Reaction notes

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