3-Chlorobenzaldehyde → 1-(3-chlorophenyl)-2,2,2-trifluoroethanol

HRID 1186349Notes

Reaction equation

HRID 1186349 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F:10][C:11]([Si](C)(C)C)([F:13])[F:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]([OH:6])[C:11]([F:13])([F:12])[F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 121848021-(3-chlorophenyl)-2,2,2-trifluoroethanolYield 136.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 3-chlorobenzaldehyde (500 mg, 3.56 mmol), (trifluoromethyl)trimethylsilane (631 μL, 4.27 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 360 μL, 0.360 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 3 hours. Thus, 1-chloro-3-(2,2,2-trifluoro-1-hydroxyethyl)benzene (Compound DB) (1.02 g, yield: quantitative) was obtained.

Workup

  1. customreacted at room temperature for 3 hours

Sources & evidence

ORD record
ord-43c84d7264514bb6821f739a4fb69a09
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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