Allyl bromide → Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

Temperature

-78 °C

9.9 ml (70.32 mmol) of diisopropylamine were initially charged in 35 ml of THF, 28.1 ml (70.32 mmol) of a 2.5 M solution of n-butyllithium in n-hexane were added at −40° C. and the mixture was stirred for 30 min. The reaction mixture was then cooled to −78° C., and a solution of 10 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 5 ml of THF was added dropwise. The mixture was stirred at −78° C. for 4 h, and a solution of 5.8 ml (66.81 mmol) of allyl bromide in 5 ml of THF was then added dropwise. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully. The mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 10.7 g (83.5% of theory) of the target compound.

1. stirringThe mixture was stirred at −78° C. for 4 h
2. temperatureThe reaction mixture was slowly warmed to RT overnight
3. extractionThe mixture was extracted three times with methyl tert-butyl ether
4. dry with materialThe combined organic phases were dried over sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-7b39fc471ba949f49c75b5e5e0fc762c

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642592B2