3-Octyn-1-ol → 1-Bromooct-3-yne

Triphenylphosphonium dibromide (36.8 g, 87.2 mmol) was suspended in diethyl ether at -20° C. and a solution of 3-octyne-1-ol (10.0 g, 79.2 mmol) was added dropwise over a twenty minute period. The mixture was allowed to stir overnight. The mixture was poured into ice-water and solids precipitated which were collected by filtration. The organic layer was separated, washed with 1N aqueous sodium hydroxide, water and dried over magnesium sulfate. The organic layer was then filtered and concentrated in vacuo to give a residue which was taken up in hexanes, filtered to remove undissolved material and concentrated to give 1-bromo-3-octyne as an orange oil (14.2 g, 96%). 1H NMR (300 MHZ) spectral data were consistent with the desired bromide (plus a trace of triphenylphosphine), and the crude product was used directly in the next step.

1. customprecipitated which
2. filtrationwere collected by filtration
3. customThe organic layer was separated
4. washwashed with 1N aqueous sodium hydroxide, water
5. dry with materialdried over magnesium sulfate
6. filtrationThe organic layer was then filtered
7. concentrationconcentrated in vacuo
8. customto give a residue which
9. filtrationfiltered
10. customto remove undissolved material
11. concentrationconcentrated

ORD record

ord-bd3b1d071b2d4e8cb73d88b16e69e4bd

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05531979