Triethylamine → 1-(Bromomethyl)-1-(trifluoromethyl)cyclopropane

Temperature

0 °C

To a solution of (1-trifluoromethyl-cyclopropyl)-methanol (1.2 g, 8.57 mmol) and Et3N (1.04 g, 10.28 mmol) in dry DMF (10 mL) at −10° C. was added methanesulfonyl chloride (981 mg, 8.57 mmol) over 20 minutes, while retaining the inner temperature at 0° C. After the addition was complete, the resulting solution was stirred at 0° C. for 30 minutes, the resulting mixture was filtered and washed with DMF (3 mL). To the combined filtrates was added sodium bromide (3.7 g, 36 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was cooled in ice, followed by addition of pentane (20 mL) and water (15 mL) while retaining the mixture at 0° C., prior to liquid separation. The organic phase was dried over Na2SO4 and filtered. The filtrate was distilled to remove the most of pentane to give 1-bromomethyl-1-trifluoromethyl-cyclopropane (0.9 g crude), which was used without further purification.

1. customat 0° C
2. additionAfter the addition
3. filtrationthe resulting mixture was filtered
4. washwashed with DMF (3 mL)
5. stirringthe resulting mixture was stirred at room temperature overnight
6. temperatureThe mixture was cooled in ice
7. customat 0° C.
8. customto liquid separation
9. dry with materialThe organic phase was dried over Na2SO4
10. filtrationfiltered
11. distillationThe filtrate was distilled
12. customto remove the most of pentane

ORD record

ord-286b9cb808a74f14accec3ccfae08b09

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102591B2