Water → HCID 57448057, compound

Temperature

-78 °C

To a solution of 1,3-dibromo-2-chlorobenzene (3.4 g, 12.6 mmol) in dry diethyl ether (60 ml), under nitrogen, at −78° C., was added dropwise n-butyllithium (2.5 M in hexane, 5.0 ml, 12.6 mmol). The mixture was stirred for 1 h after which dimethyldisulfide (1.0 ml, 13.9 mmol) was added dropwise. The resulting mixture was stirred at −78° C. for 30 min and then brought to ambient temperature. Water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (isooctane) to give the title compound (1.23 g). MS m/z (rel. intensity, 70 eV) 240 (M+, 28), 238 (M+, bp), 236 (71), 205 (29), 142 (27).

1. additionwas added dropwise
2. custombrought to ambient temperature
3. extractionthe mixture was extracted with ethylacetate (3×100 ml)
4. dry with materialThe combined organic phases was dried (MgSO4)
5. filtrationfiltered
6. customevaporated to dryness
7. customThe residue was purified by flash column chromatography (isooctane)

ORD record

ord-a964219617a74b73a657412ec5e77d39

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763639B2