Ethyl Bromide → (1-Bromoprop-2-en-1-yl)benzene

Vinylbenzyl chloride (50.60 g, 0.33 mol, 60:40 mixture of p,m isomers), sodium bromide (6.86 g, 6.67×10−2 mol), N-methylpyrrolidone (300 ml, passed through a short column of basic alumina), ethyl bromide (260 g), and 3-t-butyl-4-hydroxy-5-methyl phenyl sulfide (1.00 g, 2.79×10−3 mol) were combined in a 1 liter round bottomed flask fitted with a reflux condenser and a nitrogen inlet and the mixture was heated at reflux for 72 hours at which point the reaction was found to have proceeded to >95% conversion by gas chromatography. The reaction mixture was poured into 1 liter of water and extracted twice with 300 ml of diethyl ether. The combined ether layers were extracted twice with 1 liter of water, dried over MgSO4, and the solvents were stripped by rotary evaporation to yield yellowish oil. The crude product was purified by vacuum distillation to afford 47.5 g of product (53.1% yield).

1. customwere combined in a 1 liter round bottomed flask
2. customfitted with a reflux condenser and a nitrogen inlet
3. temperaturethe mixture was heated
4. temperatureat reflux for 72 hours at which
5. extractionextracted twice with 300 ml of diethyl ether
6. extractionThe combined ether layers were extracted twice with 1 liter of water
7. dry with materialdried over MgSO4
8. customthe solvents were stripped by rotary evaporation
9. customto yield yellowish oil
10. distillationThe crude product was purified by vacuum distillation

ORD record

ord-78604857281945c8b09d73b055df7eb0

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06537730B1