Dimethyl Sulfoxide → 6-Bromo-2-oxabicyclo[2.2.1]heptan-3-one

Temperature

0 °C

Bromotrimethysilane (3.1 mL, 0.023 mol) was added dropwise to a solution of dimethyl sulfoxide (1.6 mL, 0.023 mol) in chloroform (38.0 mL) in a round-bottom flask at 0° C. The resulting mixture was stirred at 0° C. for 2 hours. To the reaction mixture was added dropwise a solution of cyclopent-3-ene-1-carboxylic acid (2.00 g, 0.0178 mol) in chloroform (12 mL) over a period of 15 minutes and the reaction mixture was stirred at 0° C. for 10 minutes. N,N-diisopropylethylamine (4.0 mL, 0.023 mol) was then added and the resulting mixture was stirred at 0° C. After 10 minutes, the mixture was heated to reflux for 16 hours. The reaction mixture was diluted with chloroform, washed with water, brine, dried (MgSO4), and stripped in vacuo. The residue was purified by chromatography on silica gel using 30% EtOAc/hexanes as eluent to give the product. 1H NMR (400 MHz, CDCl3): δ 4.88 (brs, 1H), 4.34 (m, 1H), 2.90 (m, 1H), 2.66 (m, 1H), 2.31 (m, 1H), 1.93 (m, 1H), 1.83 (m, 1H).

1. stirringthe reaction mixture was stirred at 0° C. for 10 minutes
2. stirringthe resulting mixture was stirred at 0° C
3. waitAfter 10 minutes
4. temperaturethe mixture was heated
5. temperatureto reflux for 16 hours
6. washwashed with water, brine
7. dry with materialdried (MgSO4)
8. customThe residue was purified by chromatography on silica gel using 30% EtOAc/hexanes as eluent
9. customto give the product

ORD record

ord-ff18e2ce3c104c5ca7e389c7c019e9c1

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834022B2