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ChemicalBook CAS DataBase List 3-Bromo-4-methylbenzenesulphonamide

3-Bromo-4-methylbenzenesulphonamide synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

with bromine;iron at 20; for 1 h;

Steps:

106.1
To a mixture of p-toluenesulfonamide (2 g, 1.16 mmol) and iron (0.41 g, 7.36 mmol) was slowly added bromine (6 mL, 116 mmol). The resulting reddish brown solution was stirred at RT for 1 h. The reaction was carefully poured into ice-cold 1 M Na2S2O3 aqueous solution and extracted with CH2Cl2 (2×). The organic extracts were combined and washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. CombiFlash purification (1% to 10% MeOH/CH2Cl2) afforded the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): 7.98 (s, 1H), 7.71 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.54 (br s, 2H), 2.41 (s, 3H).

References:

Amgen Inc. US2006/199817, 2006, A1 Location in patent:Page/Page column 53

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