Bromobenzene → 1309602-18-3

Temperature

0 °C

Under N2, 60% NaH (10.2 g, 254.27 mmol) and 40 mL DMF were added into a 500 mL reaction flask and cooled to 0° C. 2,2-difluoroethanol 12a (23 g, 280.3 mmol) was dissolved in 40 mL DMF and then dropwise added into the mixture within 4 hours at 0° C. The reaction mixture was then warmed to room temperature. After 30 minutes, a solution of bromobenzene (39.92 g, 254.25 mmol) in DMF (40 mL) and CuBr (0.35 g, 2.43 mmol) were added in turn before the reaction mixture was warmed and stirred for 16 hours at 160° C. Thereafter, the reaction mixture was cooled to room temperature and filtered. The filtrate was washed with n-hexane. 5% hydrochloric acid (160 mL) was added to the filtrate before the resulting residue was extracted with n-hexane (160 mL×3). The organic extract was washed with saturated sodium chloride solution (50 mL) and combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound 2,2-difluoroethoxybenzene 12c (32.97 g, yellow liquid), yield: 82.0%.

1. additiondropwise added into the mixture within 4 hours at 0° C
2. temperatureThe reaction mixture was then warmed to room temperature
3. temperaturewas warmed
4. temperatureThereafter, the reaction mixture was cooled to room temperature
5. filtrationfiltered
6. washThe filtrate was washed with n-hexane
7. addition5% hydrochloric acid (160 mL) was added to the filtrate before the resulting residue
8. extractionwas extracted with n-hexane (160 mL×3)
9. extractionThe organic extract
10. washwas washed with saturated sodium chloride solution (50 mL)
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-2ae47fdf6a2a4696bf738234b9bc3f03

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2