2,2,2,4'-Tetrafluoroacetophenone → 2,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane (Example II) (1.72 g, 5.0 mmol) in tetrahydrofuran (12 ml) under a nitrogen atmosphere was slowly added a solution of n-butyl lithium in hexanes (1.6 M) (3.3 ml, 5.28 mmol) at −70° C. The reaction mixture was stirred at −70° C. for 30 minutes before addition of 2,2,2,4′-tetrafluoroacetophenone (commercially available) (1.01 g, 5.25 mmol) at −70° C. The cooling bath was removed after 15 minutes. Once the reaction mixture had reached ambient temperature, it was poured onto water. The mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over sodium sulfate, and then concentrated. The title compound was isolated as a yellow oil.

1. customThe cooling bath was removed after 15 minutes
2. customhad reached ambient temperature
3. additionit was poured onto water
4. extractionThe mixture was extracted with diethyl ether
5. washThe organic phase was washed with water and brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-fd90c40e3b4d43f995710731cd943f44

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618173B2