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0 °C

A mixture of tosyl bromide (1.82 g, 7.76 mmol), Et3N (1.08 mL, 7.76 mmol), and CCl4 (15 mL) was cooled to 0° C. and treated with a solution of 2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-benzenethiol (prepared in Example III; 1.94 mmol) in CCl4 (15 mL) via addition funnel over a period of 45 minutes. The mixture was then allowed to warm to room temperature where it was stirred for 4 days. The mixture was diluted with CH2Cl2 and quenched with saturated NH4Cl. The layers were separated, the organic layer dried (Na2SO4) and the solvent removed in vacuo. The residue was submitted to column chromatography (3:1 hexanes:CH2Cl2 to 1:1 hexanes:CH2Cl2) to provide the title compound. 1H NMR (CDCl3) δ 0.0 (s, 6 H), 0.78 (s, 9 H), 0.97 (s, 9 H), 1.84 (s, 3 H), 2.18 (s, 3 H), 6.60 (s, 1 H), 6.94-7.02 (m, 4 H), 7.25 (s, 1 H).

1. temperatureto warm to room temperature where it
2. customquenched with saturated NH4Cl
3. customThe layers were separated
4. dry with materialthe organic layer dried (Na2SO4)
5. customthe solvent removed in vacuo