Thionyl Chloride → 1-Chloro-4-{[4-(1-chloroethyl)phenyl]oxy}-2-(trifluoromethyl)benzene

HRID 474615Notes

Reaction equation

HRID 474615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15](O)[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([Cl:24])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 677755811-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol

Product 1

HCID 677734481-Chloro-4-{[4-(1-chloroethyl)phenyl]oxy}-2-(trifluoromethyl)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 1-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol (50 mg, 0.158 mmol) in DCM (1.5 mL), was added thionyl chloride (0.1 mL, 1.378 mmol) dropwise. The mixture was stirred at room temperature for 1 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice, dried over Na2SO4, and concentrated in vacuo to afford the title compound (50 mg, 95% yield). LCMS: rt=3.63 min, [M+H+]=299

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a5ae6df99c54a96918017ff26ccdf6f
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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