Hydrogen Bromide → (2-Bromoethyl)cyclohexane

To a solution of 10 g of (2-hydroxyethyl)cyclohexane in 50 ml of dry diethyl ether was added dropwise a solution of 9.85 g of phosphorous tribromide in 20 ml of dry diethyl ether at -40° C., and the mixture was stirred at -40° to -10° C. for 30 minutes and at 2° to 4° C. for 2.5 hours. The reaction mixture was then poured into ice-water and extracted with diethyl ether. The extract was washed with water, an aqueous solution of sodium bicarbonate and water, dried over magnesium sulphate and concentrated under reduced pressure. To the residue thus obtained were added 50 ml of 47% w/v hydrobromic acid at -30° C. 20 ml of sulphuric acid were then added dropwise at the same temperature. The reaction mixture was refluxed at 100° to 110° C. for 3 hours and extracted with diethyl ether. The extract was washed with water, an aqueous solution of sodium bicarbonate and water, dried over magnesium sulphate and concentrated under reduced prssure. The residue was purified by distillation under reduced pressure to give 8.04 g of the title compound having the following physical characteristics:

1. extractionextracted with diethyl ether
2. washThe extract was washed with water
3. dry with materialan aqueous solution of sodium bicarbonate and water, dried over magnesium sulphate
4. concentrationconcentrated under reduced pressure
5. customTo the residue thus obtained
6. additionwere added 50 ml of 47%
7. customat -30° C
8. temperatureThe reaction mixture was refluxed at 100° to 110° C. for 3 hours
9. extractionextracted with diethyl ether
10. washThe extract was washed with water
11. dry with materialan aqueous solution of sodium bicarbonate and water, dried over magnesium sulphate
12. concentrationconcentrated under reduced prssure
13. distillationThe residue was purified by distillation under reduced pressure

ORD record

ord-b1aeb3861d16427d8d57bf28c6e50af3

Source dataset

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04178367