Tetrahydrofuran → 6'-Bromospiro[cyclopropane-1,2'-inden]-1'(3'H)-one

Temperature

-78 °C

A dried flask was charged with 1-(4-bromo-2-iodobenzyl)cyclopropanecarbonitrile (Intermediate 51, 3.29 g, 9.09 mmol) and dry THF (30 mL) was added under argon atmosphere. The resulting mixture was cooled to −78° C. and n-BuLi (2.5 M in hexanes, 7.27 mL, 18.2 mmol) was added dropwise. The solution was allowed to reach r.t. The reaction was quenched with MeOH (2 mL) and HCl (1M, 5 mL). The mixture was extracted with EtOAc. The water phase was basified with sat NaHCO3 and extracted with EtOAc twice. The organic phases were combined, dried over MgSO4, filtered and concentrated in vacuo. HCl (1 M, 4 mL) and DCM (5 mL) were added and the organic phase was collected. This was repeated twice. The water phase was basified with sat NaHCO3 and extracted with DCM. The combined organic phases were dried through a phase separator and evaporated to dryness to give the title compound (1.1 g, 51% yield): MS (CI) m/z 237 [M+H]+.

1. additionwas added under argon atmosphere
2. customto reach r.t
3. customThe reaction was quenched with MeOH (2 mL) and HCl (1M, 5 mL)
4. extractionThe mixture was extracted with EtOAc
5. extractionextracted with EtOAc twice
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. additionHCl (1 M, 4 mL) and DCM (5 mL) were added
10. customthe organic phase was collected
11. extractionextracted with DCM
12. customThe combined organic phases were dried through a phase separator
13. customevaporated to dryness

ORD record

ord-aa272618184e47548f67b41959c2fa0f

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415483B2