Carbon tetrabromide → HCID 18177915, compound

Temperature

0 °C

1.62 g of carbon tetrabromide were dissolved in 25 ml of methylene chloride and treated, at −20° C., with a solution of 2.56 g of triphenylphosphine in 25 ml of methylene chloride. The mixture was stirred at 0° C. for 15 minutes. To the orange solution were added 733 mg of (RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-heptanal in 4 ml of methylene chloride, at 0° C. The reaction mixture was stirred at room temperature for 4 hours. The mixture was quenched with the addition of 50 ml of water followed by 6 ml of a saturated aqueous sodium bicarbonate solution. The phases were separated and the aqueous phase was further extracted with 2 portions of 25 ml of methylene chloride. The combined organic extracts were dried over MgSO4 and concentrated in vacuo, giving a yellow solid. The residue was triturated in pentane and the solid was removed by filtration. The filtrate was concentrated in vacuo, yielding a yellow oil which was purified by flash chromatography (SiO2, hexane), giving 1.03 g of (RS)-1,1-dibromo-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-oct-1-ene, as a colorless oil.

1. customat 0° C
2. stirringThe reaction mixture was stirred at room temperature for 4 hours
3. customThe mixture was quenched with the addition of 50 ml of water
4. customThe phases were separated
5. extractionthe aqueous phase was further extracted with 2 portions of 25 ml of methylene chloride
6. dry with materialThe combined organic extracts were dried over MgSO4
7. concentrationconcentrated in vacuo
8. customgiving a yellow solid
9. customThe residue was triturated in pentane
10. customthe solid was removed by filtration
11. concentrationThe filtrate was concentrated in vacuo
12. customyielding a yellow oil which
13. customwas purified by flash chromatography (SiO2, hexane)

ORD record

ord-3d08a48898e84cb4a2f853671c36cf71

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06603012B2