Phosphorus tribromide → (4-Bromobutyl)cyclohexane

Temperature

0 °C

4-Cyclohexyl-butan-1-ol(8.1 ml, 47 mmol) at -5° C. under nitrogen was treated dropwise over 10-15 min with 2.2 ml (23 mmol) of phosphorus tribromide, stirred at 0° C. for 15 min, room temperature for 2 h, then at 100° C. for 1.5 h before cooling to 0° C. The reaction was quenched with 50 g of ice, diluted with 100 ml of brine, and extracted with ether. The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and distilled at 2 mm Hg, 100° C., to give 9.84 g (96%) of 1-bromo-4-cyclohexylbutane as a colorless liquid. NMR (CDCl3, TMS) δ 0.6-2.3 (m, 17H), 3.43 (t, J=7 Hz, 2H).

1. temperatureat 100° C. for 1.5 h before cooling to 0° C
2. customThe reaction was quenched with 50 g of ice
3. additiondiluted with 100 ml of brine
4. extractionextracted with ether
5. washThe combined organics were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. distillationdistilled at 2 mm Hg, 100° C.

ORD record

ord-3b668845450245ec83f9ca136b493a30

Source dataset

uspto-grants-1987_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04683330