3,5-Dichlorobenzaldehyde → 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6].[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C:12]([F:14])([F:13])[F:11])[CH:7]=[C:8]([Cl:10])[CH:9]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in THF (250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with water and was extracted with ethyl acetate (EtOAc; 3×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).
Workup
- stirringwas stirred for 16 h
- extractionwas extracted with ethyl acetate (EtOAc; 3×)
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e8388f5ad62549a6877c6ed47f931c30
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09211281B2
Reaction notes
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