Thionyl Chloride → HCID 20343965, compound

HRID 2049867Notes

Reaction equation

HRID 2049867 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15]O)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][Cl:3])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 541878152-[(4-Fluorophenyl)thio]benzenemethanol

Product 1

HCID 20343965HCID 20343965, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

8.5 g of thionyl chloride are added dropwise over a 10 minute span to a stirring mixture of 13.0 g of 2-(4-fluorophenylthio)benzyl alcohol in 80 ml of benzene at ambient temperature. After total addition, the reaction mixture is stirred for 16 hours before being carefully poured onto 350 ml of crushed ice containing 8 g of sodium bicarbonate. The mixture is stirred until the ice melts. The layers separate and the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution, washed twice with 40 ml portions of water, washed once with 25 ml of saturated sodium chloride solution, dried and rotary evaporated to provide 2-(4-fluorophenylthio)benzyl chloride.

Workup

  1. additionAfter total addition
  2. customThe layers separate
  3. washthe benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution
  4. washwashed twice with 40 ml portions of water
  5. washwashed once with 25 ml of saturated sodium chloride solution
  6. customdried
  7. customrotary evaporated

Sources & evidence

ORD record
ord-dd0ee71313bf4776939787192fa858cf
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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