Diphenyl sulfide → 4-Chloro-2-(difluoromethoxy)phenol

HRID 2359304Notes

Reaction equation

HRID 2359304 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[Cl-].[Cl-].[Cl-].[Al+3].S(C1C=CC=CC=1)C1C=CC=CC=1.S(Cl)([Cl:32])(=O)=O>ClCCl>[Cl:32][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([O:3][CH:2]([F:11])[F:1])[CH:9]=1

Participants

6

Reactant 4

HCID 8766Diphenyl sulfideHCID 24648Sulfuryl chlorideHCID 27741212-(Difluoromethoxy)phenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 600510324-Chloro-2-(difluoromethoxy)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold suspension of 2-(difluoromethoxy)phenol (6.54 g, 0.00408 mol), aluminum trichloride (0.0544 g, 0.000408 mol) and 1,1′-thiodibenzene (0.068 mL, 0.000408 mol) was added sulfuryl dichloride (3.61 mL, 0.0449 mmol) dropwise. The reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction was diluted in dichloromethane (10.0 mL) and purified using silica gel column chromatography eluting with 0-20% EtOAc in heptane. The title compound was isolated as a colourless oil (2.33 g, 0.01195 mol, 29%).

Workup

  1. custompurified
  2. washeluting with 0-20% EtOAc in heptane

Sources & evidence

ORD record
ord-d39ec5b0deb14b79b960b8f2276bf427
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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