Ethyl vinyl ether → 2-Bromo-4-(1-ethoxy-ethoxy)-but-1-ene

While cooling a solution of 10.38 g (0.0687 mol) of 3-bromo-3-buten-1-ol in 20 ml of diethyl ether with 50 mg (0.000263 mol) p-toluene sulfonic acid monohydrate in an ice water bath, 19 ml (0.199 mol) of ethyl vinyl ether was added slowly dropwise to maintain an internal temperature of <10° C. After 1 hour at 0° C., a few drops of triethylamine was added. The reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The isolated organic layer was washed with brine then dried over potassium carbonate and filtered. The solvent was removed from the filtrate in vacuo to yield 14.04 g of 2-bromo-4-(1-ethoxy-ethoxy)-but-1-ene as an oil.

1. temperatureto maintain an internal temperature of <10° C
2. additionThe reaction mixture was poured onto water
3. customThe resulting mixture was transferred to a separatory funnel
4. customthe phases were separated
5. washThe isolated organic layer was washed with brine
6. dry with materialthen dried over potassium carbonate
7. filtrationfiltered
8. customThe solvent was removed from the filtrate in vacuo

ORD record

ord-76ebaf9507254ae199d91d59c0e642b1

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548448B2