Thionyl Chloride → 4-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether

HRID 536159Notes

Reaction equation

HRID 536159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].S(Cl)([Cl:23])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Cl:23])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66825563(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol

Product 1

HCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherYield 94.2%

Procedure

A solution of (4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methanol (200 mg, 0.661 mmol) in thionyl chloride (0.5 mL, 6.85 mmol) was stirred at rt for 1 h. Then the excess thionyl chloride was removed under vacuum to afford the title product (200 mg) as a yellow oil, which was used in the next reaction without purification. LC-MS (ESI): m/z 285 [M−Cl]+; 4.17 min (ret time).

Workup

  1. customThen the excess thionyl chloride was removed under vacuum

Sources & evidence

ORD record
ord-1b74d965a312488283ca2a20982b7f1d
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

Loading…