Lithium Bromide → 4-(2-Bromoethyl)oxane

To a stirring solution of 2-(4-oxanyl)ethyl methanesulfonate (11.9 g, 56.9 mmol) in dry acetone (300 mL) was added lithium bromide (29.7 g, 56.9 mmol). The reaction was refluxed under an N2 atmosphere for 5 h. The acetone was removed by rotary evaporation, water (150 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The combined extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to yield a light brown oil. The crude compound was then distilled (65° C., 0.2 mm) to yield 8.06 g of a colorless oil (73.3% yield).

1. temperatureThe reaction was refluxed under an N2 atmosphere for 5 h
2. customThe acetone was removed by rotary evaporation, water (150 mL)
3. additionwas added
4. extractionthe mixture was extracted with dichloromethane (2×100 mL)
5. dry with materialThe combined extracts were dried (K2CO3)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. customto yield a light brown oil
9. distillationThe crude compound was then distilled (65° C., 0.2 mm)

ORD record

ord-7add135abfc94a6cb645efbd43ea1482

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214686B2