Phenacyl bromide → HCID 58122284, compound

Temperature

-78 °C

1.36 g (−)-β-pinene (10 mmol) was dissolved in 5 ml THF. 21 ml of a 0.5-molar solution of 9-BBN in THF (10.5 mmol) was added to this solution at 0° C. The reaction mixture was slowly brought to room temperature and stirred for a further 3 hours. The resulting solution was cooled to −78° C., and a solution of 1.12 g potassium tert-butanolate (10 mmol) in 10 ml THF was then added to the cooled reaction solution. After a short time, 2 g α-bromacetophenone (10 mmol) was added in portions with constant stirring. The reaction mixture was slowly brought to room temperature and stirred for 4 hours at room temperature. The resulting product mixture had 50 ml n-pentane added to it, and washed three times in each case with 10 ml of a 3N sodium hydroxide solution and with 10 ml water. The organic phase was dried over magnesium sulfate. Solvent was removed from the filtrate at reduced pressure. The raw product was purified by column chromatography. 140 mg (10%) of the aforesaid product was obtained.

1. customwas slowly brought to room temperature
2. customwas slowly brought to room temperature
3. stirringstirred for 4 hours at room temperature
4. additionadded to it
5. washwashed three times in each case with 10 ml of a 3N sodium hydroxide solution
6. dry with materialThe organic phase was dried over magnesium sulfate
7. customSolvent was removed from the filtrate at reduced pressure
8. customThe raw product was purified by column chromatography

ORD record

ord-fa3189d1930146958585c97ac67d331d

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129569B2