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A mixture of 27 g of N-(1,1-dimethylethyl)-2-methoxy-5-methylbenzenesulfonamide (E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 603), 19.6 g NBS and 0.3 g azobisisobutyronitrile in 200 ml CH2Cl2 was refluxed and illuminated with a sun lamp. After 8 hours the lamp was turned off and the reaction was refluxed for another 24 hr. The reaction was allowed to cool. The reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine:sodium sulfite-sodium bicarbonate-water. The organic layer was dried (MgSO4), treated with charcoal and filtered through a 5 g plug of silica gel. The plug was washed with 100 ml of chloroform. The combined organic fractions were evaporated to give 34 g of solid, m.p. 137°-142° C.;

1. temperaturewas refluxed
2. customilluminated with a sun lamp
3. temperaturethe reaction was refluxed for another 24 hr
4. temperatureto cool
5. washThe reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine
6. dry with materialThe organic layer was dried (MgSO4)
7. additiontreated with charcoal
8. filtrationfiltered through a 5 g plug of silica gel
9. washThe plug was washed with 100 ml of chloroform
10. customThe combined organic fractions were evaporated