(-)-Epichlorohydrin → HCID 67073079, compound

Temperature

-100 °C

The solution of 1.1 g (4.6 mmol) 4-bromo-2-chloro-1-methylsulfanyl-benzene (e.g. Joshi, R. S et. al.; J. Karnatak University (1959), 4, 38-42) in 40 mL diethyl ether was cooled down to −115° C. Then, 3.0 mL tert-butyllithium (4.5 mmol; 1.5M solution in n-pentane) was added dropwise and after stirring for 50 min. at −100° C. 0.54 mL (6.9 mmol) (R)-(−)-epichlorohydrin was added. After 45 min. the reaction was allowed to warm to 0° C. and after another 1.5 h was quenched with water and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed using MPLC and tert-butyl methyl ether: n-heptane (1:2 v/v) as eluant to give the compound as a colorless oil (35%).

1. waitAfter 45 min. the reaction was allowed
2. temperatureto warm to 0° C. and after another 1.5 h
3. customwas quenched with water
4. extractionextracted three times with ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was chromatographed

ORD record

ord-856e70fd5a594fc19df17acdb773be1c

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323466B2