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16th June 2014 @ 15:54

The previous reaction Synthesis of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-methylbenzenesulfonamide (PT-1-20) was repeated on 0.25x scale with the semi-purified (but hopefully sulfur-free product from Resynthesis of 3-bromo-4-methyl-benzenesulfonamide (PT-17-2).

3-bromo-4-methylbenzenesulfonamide (280 mg), bis(pinacolato)diboron (427 mg), potassium acetate (440 mg) was dissolved in 1,4-dioxan (6 mL) and degassed with argon for ten minutes. Pd(dppf)2.CH2Cl2 (46 mg) was added and the reaction heated to 100°C in a sealed tube for 16 hours. The reaction mixture was diluted with methanol (20 mL) and dichloromethane (20 mL) and treated with activated carbon then filtered through celite and evaporated to give a dark solid. NMR indicated the same material as previous, with signals corresponding to pinacol but no arylboronate. Could be the dimer?

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