Tetramethylammonium fluoride → 4-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2,6-dimethyl-benzonitrile

HRID 2096850Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:23])[C:11]([C:13]1[CH:20]=[C:19]([CH3:21])[C:16]([C:17]#[N:18])=[C:15]([CH3:22])[CH:14]=1)=[O:12].[F:24][C:25]([Si](C)(C)C)([F:27])[F:26].[F-].C[N+](C)(C)C>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:23])[C:11]([C:13]1[CH:14]=[C:15]([CH3:22])[C:16]([C:17]#[N:18])=[C:19]([CH3:21])[CH:20]=1)([OH:12])[C:25]([F:27])([F:26])[F:24]

Participants

Reactant 3

HCID 67803Tetramethylammonium fluoride

HCID 552549(Trifluoromethyl)trimethylsilane

HCID 666970254-[2-(2-Chloro-4-methoxy-phenyl)-propionyl]-2,6-dimethyl-benzonitrile

Product 1

HCID 666970754-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2,6-dimethyl-benzonitrile

Procedure

In analogy to Example 1, step 3, 4-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-2,6-dimethyl-benzonitrile was reacted with (trifluoromethyl)trimethylsilane and tetramethylammonium fluoride to give the title compound as a colorless solid. MS (m/e, ISP neg. ion)=395.9 [M−H+].

Sources & evidence

ORD record: ord-7da61993451345a0aa91ee0ba464b2a1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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