Hydrochloric Acid → HCID 178459137, compound

Temperature

-78 °C

1-Iodo-3,3-difluoropropanyl boronate pinacol (2.7 g, 8.1 mmol) was dissolved in THF (10 mL) and was added dropwise to a solution of lithium bis(trimethylsilyl)amide (9.68 mL, 9.68 mmol, 1.0 M in THF) dissolved in anhydrous THF (10 mL) and cooled to −78° C. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. It was concentrated in vacuo and hexane was added. The reaction mixture was cooled to −78° C., followed by the dropwise addition of 4 N anhydrous hydrogen chloride in dioxane (6.05 mL, 24.2 mmol). The mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction mixture was evaporated and chloroform was added. Insoluble material was removed by filtration. The filtrate was evaporated almost to dryness and hexanes were added. Upon standing the product crystallized. It was isolated and washed with cold hexane to yield 1.1 g (52%), mp 138-141° C. 1H NMR (CDCl3) δ 7.68 (bs, 3H), 6.22-6.01 (tt, 1H), 3.42 (m, 1H), 2.76-2.51 (m, 2H), 1.32 (s, 12H). 19F NMR δ −115.2 to −115.5 (dt, CHF2). HRMS calculated for C9H18B1O2F2N+H: 222.1. Found: 222.1.

1. temperatureto warm to room temperature
2. concentrationIt was concentrated in vacuo and hexane
3. additionwas added
4. temperatureThe reaction mixture was cooled to −78° C.
5. temperatureto warm to room temperature
6. stirringstirred for 5 hours
7. customThe reaction mixture was evaporated
8. additionchloroform was added
9. customInsoluble material was removed by filtration
10. customThe filtrate was evaporated almost to dryness and hexanes
11. additionwere added
12. customcrystallized
13. customIt was isolated
14. washwashed with cold hexane
15. customto yield 1.1 g (52%), mp 138-141° C

ORD record

ord-62910c5f56784f38984e7fa35416adfd

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122627B2