Dimethyl Sulfoxide → HCID 58920887, compound

To a 50 mL flask flushed with nitrogen, equipped with a stir bar was added potassium tertbutoxide (1.1 g, 10 mmol, 95%). DMSO was added (10 mL) followed by addition of a solution of 2,2,3,3-tetrafluoropropan-1-ol (0.95 mL, 11 mmol) via syringe. After 5 min, 1-bromo-3,5-difluorobenzene (1.1 mL, 9.5 mmol) was added and the reaction mixture stirred at room temperature for 18 h. Water was added (100 mL), and the aqueous phase extracted with ether (2×100 mL). The organic portion was then washed successively with water (2×100 mL) and saturated NaCl solution (2×100 mL), dried over Na2SO4, decanted and concentrated under reduced pressure yielding a crude yellow liquid which was purified by distillation under reduced pressure at 140° C. yielding the 1-Bromo-3-fluoro-5-(2,2,3,3-tetrafluoropropoxy)benzene as a colorless oil (1.6 g, 54% yield).

1. customTo a 50 mL flask flushed with nitrogen
2. customequipped with a stir bar
3. extractionthe aqueous phase extracted with ether (2×100 mL)
4. washThe organic portion was then washed successively with water (2×100 mL) and saturated NaCl solution (2×100 mL)
5. dry with materialdried over Na2SO4
6. customdecanted
7. concentrationconcentrated under reduced pressure
8. customyielding a crude yellow liquid which
9. distillationwas purified by distillation under reduced pressure at 140° C.

ORD record

ord-942f0504065943c68991b0862fd358f8

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888376B2