Thionyl Chloride → 1-(Chloromethyl)-3-(4-(trifluoromethyl)phenoxy)benzene

HRID 1666423Notes

Reaction equation

HRID 1666423 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:16]=[CH:17][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23136407(3-(4-(Trifluoromethyl)phenoxy)phenyl)methanol

Product 1

HCID 668759551-(Chloromethyl)-3-(4-(trifluoromethyl)phenoxy)benzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-(4-(Trifluoromethyl)phenoxy)phenyl)methanol from Step 1 (1.3 g, 4.85 mmol), in dichloromethane (10 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (0.39 mL, 5.33 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 16 h. The reaction was concentrated by evaporation and the residue was purified by silica gel chromatography (0-20%, EtOAc:heptane) to afford the title compound (1.34 g) as a thick oil.

Workup

  1. concentrationThe reaction was concentrated by evaporation
  2. customthe residue was purified by silica gel chromatography (0-20%, EtOAc:heptane)

Sources & evidence

ORD record
ord-5cd0d9a3c3a743828efd325dca491bbb
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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