Water → HCID 13920898, compound

Temperature

-10 °C

Liquified methylamine (36.3 mL, 0.817 mol) was added slowly to a stirred solution of 2-bromobenzenesulfinyl chloride (48.9 g, 0.204 mol) in dichloromethane (489 mL) cooled below -70° C. The reaction mixture was allowed to warm to -10° C. and was then shaken with water (489 mL). The layers were separated, and the dichloromethane layer was washed with water (2×245 mL), dried (Na2SO4), and filtered. Evaporation of the solvent left a pale yellow oil (44.4 g) that mostly crystallized on standing. This was dissolved in dichloromethane and chromatographed on a column of silica gel using 2:1 dichloromethane-ether as eluant. Fractions containing product (Rf =0.52, UV) were evaporated to leave 2-bromo-N-methylbenzenesulfinamide as a white crystalline solid (39.5 g) melting at 66°-70° C.

1. temperaturecooled below -70° C
2. customThe layers were separated
3. washthe dichloromethane layer was washed with water (2×245 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customEvaporation of the solvent
7. waitleft a pale yellow oil (44.4 g) that
8. custommostly crystallized
9. dissolutionThis was dissolved in dichloromethane
10. customchromatographed on a column of silica gel using 2:1 dichloromethane-ether as eluant
11. additionFractions containing product (Rf =0.52, UV)
12. customwere evaporated

ORD record

ord-227972f08d6e43188ad3c1fd22ad9b59

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04705555