Thionyl Chloride → 4-(Chloromethyl)-2-(trifluoromethyl)-1-{[3-(trifluoromethyl)phenyl]oxy}benzene

HRID 474629Notes

Reaction equation

HRID 474629 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH2:20]O)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.S(Cl)([Cl:26])=O>C(Cl)Cl>[Cl:26][CH2:20][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[C:3]([C:2]([F:23])([F:22])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86666206(3-(Trifluoromethyl)-4-(3-(trifluoromethyl)phenoxy)phenyl)methanol

Product 1

HCID 866662074-(Chloromethyl)-2-(trifluoromethyl)-1-{[3-(trifluoromethyl)phenyl]oxy}benzeneYield 109%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (3-(trifluoromethyl)-4-{[3-(trifluoromethyl)phenyl]oxy}phenyl) methanol (300 mg, 0.892 mmol) in DCM (4 mL) was added thionyl chloride (0.130 mL, 1.784 mmol) dropwise under nitrogen. The mixture was stirred at room temperature for 2 h. The mixture was stirred at room temperature for 2 h. The reaction was quenched with water, adjusted pH about 7 and extracted with DCM. The organic layer was separated and concentrated to afford the crude title compound (430 mg, 0.970 mmol, 109% yield) which can be used in next step directly.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customThe reaction was quenched with water, adjusted pH about 7
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ebe4c44b815c4695a1571c3e1941c028
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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