Hydrochloric Acid → 604787-90-8

Temperature

-78 °C

A solution of 8.36 g of 1-bromomethyl-4-(2,2-dibromovinyl)cyclohexane (trans/cis=about 3/1) in 20 mL of tetrahydrofuran was cooled to −78° C. under a nitrogen atmosphere. To the solution was added dropwise 24.3 mL of a 2.1 M methyl lithium diethyl ether solution over 30 minutes, followed by stirring for 2 hours while maintaining a temperature of −78° C. The reaction mixture was cooled in an ice bath, and 30 mL of a 1 N aqueous hydrochloric acid solution was added thereto. The reaction mixture was extracted with 30 mL of t-butyl methyl ether three times. The combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4.68 g of 1-bromomethyl-4-ethynylcyclohexane represented by the following formula:

1. temperatureThe reaction mixture was cooled in an ice bath
2. extractionThe reaction mixture was extracted with 30 mL of t-butyl methyl ether three times
3. washThe combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-f879d57edc32481eb6f90b8518df2e86

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344163B2