Hydrogen Bromide → (Bromomethyl)cyclooctane

Temperature

130 °C

Cyclooctylmethanol (8.16 g) was dissolved in 47% HBr-solution (70 ml) and refluxed for 1 hour at 130° C. The reaction mixture was poured onto icewater (500 ml) and saturated sodium hydrogencarbonate solution (500 ml) was added. The aqueous solution was extracted with dichloromethane. The combined organic phases were washed with water, brine and dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel in toluene as eluent. The fractions containing cyclo-octylmethyl bromide were pooled and evaporated. Yield: 9.85 g. TLC: Rf=0.95, silica gel, toluene

1. additionwas added
2. extractionThe aqueous solution was extracted with dichloromethane
3. washThe combined organic phases were washed with water, brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was chromatographed on silica gel in toluene as eluent
8. additionThe fractions containing cyclo-octylmethyl bromide
9. customevaporated

ORD record

ord-8688ad55586a4226b9f1d0d221162413

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06432921B1