Tetrahydrofuran → 1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol

To a solution of 2-bromo-2-thiophenecarboxaldehyde (2.1 g, 0.01 mol) and trimethyl(trifluoromethyl)silane (1.7 g, 0.012 mol) in dry tetrahydrofuran at 0° C. was added tetrabutylammonium fluoride (10 mL of 1.0 M tetrahydrofuran solution, 0.01 mol) drop wise. The mixture was warmed to room temperature and stirred for 36 hours. The reaction was then quenched with 6N HCl and stirred for 30 minutes, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to give 3.3 g of crude as a dark brown oil, which was purified through a plug of silica gel eluting with an ethyl acetate and hexane mixture (1:1) to give 2.56 g of the title compound as a yellow liquid (98% yield), 1H NMR (300 MHz, CDCl3) δ ppm 2.78 (d, J=5.15 Hz, 1H) 5.14-5.27 (m, 1H) 6.95 (d, J=3.68 Hz, 1H) 7.00 (d, J=3.68 Hz, 1H),

1. customThe reaction was then quenched with 6N HCl
2. stirringstirred for 30 minutes
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. customto give 3.3 g of crude as a dark brown oil, which
9. customwas purified through a plug of silica gel eluting with an ethyl acetate and hexane mixture (1:1)

ORD record

ord-c86f585868fd48adadb98aa7ad99516a

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748627B2