Thionyl Chloride → HCID 20513414, compound

HRID 1164119Notes

Reaction equation

HRID 1164119 reaction equation
[CH3:1][O:2][C:3]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:17](O)[CH3:18].S(Cl)([Cl:22])=O>N1C=CC=CC=1.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH:17]([Cl:22])[CH3:18])=[CH:5][CH:6]=[CH:7][C:8]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20513492HCID 20513492, compound

Product 1

HCID 20513414HCID 20513414, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1-[2-methoxy-3-(2-fluorophenylthio)phenyl]ethanol (1 g), thionyl chloride (500 mg) and pyridine (2 drops) in benzene (30 ml) was refluxed under heating for 30 minutes. The reaction mixture was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with diethyl ether. The extract was washed with dil. hydrochloric acid, saturated aqueous sodium bicarbonate and water in turn, dried and then evaporated under reduced pressure to give oily 2-fluorophenyl 2-methoxy-3-(1-chloroethyl)phenyl thioether (850 mg).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 30 minutes
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract was washed with dil. hydrochloric acid, saturated aqueous sodium bicarbonate and water in turn
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39488eb2acaf4e0290735c60732e7e12
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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