Acetyl bromide → 1-Bromobicyclo(2.2.2)octane

Temperature

0 °C

To a stirred mixture of 1-methoxybicyclo[2.2.2]octane (4.0 g, 28 mmol) and acetyl bromide (6.2 g, 50.4 mmol) was added 10 drops of stannic chloride at 0° C. After stirring for 0.5 h, the temperature was allowed to rise to 20-25° C. and stirring was continued at the same temperature for 3 h. After cooling to 0° C., water (30 mL) was added and the mixture was stirred for 10 min. Then the mixture was poured into water (150 mL) and extracted with ether (100 mL×3). The ether layers were combined, washed with aqueous sodium bicarbonate and water, and dried over sodium sulfate. The solvent was removed under reduced pressure to produce 1-bromobicyclo[2.2.2]octane (4.0 g, 75%), which was used for next step without purification. 1H NMR (CDCl3) δ 2.23 (m, 6H), 1.95 (m, 1H), 1.81-1.63 (m, 6H), 1.52 (m, 1H).

1. customto rise to 20-25° C.
2. stirringstirring
3. waitwas continued at the same temperature for 3 h
4. stirringthe mixture was stirred for 10 min
5. extractionextracted with ether (100 mL×3)
6. washwashed with aqueous sodium bicarbonate and water
7. dry with materialdried over sodium sulfate
8. customThe solvent was removed under reduced pressure

ORD record

ord-acc71d7fc0854810b99d7a7769d070f4

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08487108B2