1-Bromo-2-Chloroethane → HCID 23001007, compound

Temperature

-78 °C

Diisopropylamine (2.71 ml, 1.1 eq.) was added to dry THF (10 ml) and cooled to -78° C. N-Butyllithium (11.01 ml of 1.6 Molar solution, 1.0 eq.) was added and the mixture stirred at -78° C. for 0.5 hour. To this mixture was then added dropwise a solution of ethyl-2-cyclohexylacetate (3.0 g, 1.0 eq.) in THF (20 ml) at -78° C. and stirred for 0.5 hour. DMPU (2.13 ml, 1.0 eq.) in THF (20 ml) was added dropwise and allowed to stir at -78° C. for 10 minutes. To this mixture was added 1-bromo-2-chloroethane (1.46 ml, 1.0 eq.) in THF (10 ml) and the mixture stirred at -5° C. for 15 minutes. The mixture was then warmed to room temperature and stirred for 1.0 hour. The mixture was cooled to 0° C., quenched with saturated ammonium chloride solution, extracted with ethyl ether and the ether layer was washed three times with water. The organic layer was separated, dried over K2CO3 and the solvent removed to provide 3.6 g of product. This was fractionally distilled to provide 3.0 g of product Boiling Point 66°-70° C. at 0.05 mmHg.

1. stirringstirred for 0.5 hour
2. stirringto stir at -78° C. for 10 minutes
3. stirringthe mixture stirred at -5° C. for 15 minutes
4. temperatureThe mixture was then warmed to room temperature
5. stirringstirred for 1.0 hour
6. temperatureThe mixture was cooled to 0° C.
7. customquenched with saturated ammonium chloride solution
8. extractionextracted with ethyl ether
9. washthe ether layer was washed three times with water
10. customThe organic layer was separated
11. dry with materialdried over K2CO3
12. customthe solvent removed

ORD record

ord-b21afd45fa134ba6a1445fa76a415371

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250542