Benzenesulfonyl chloride, 2-bromo-5-chloro-4-methoxy- synthesis

Yield:868406-66-0 72%

Reaction Conditions:

with chlorosulfonic acid at 0 - 20;

Steps:

30.a

Example 30: 5-Chloro-2-((E)-3-13-(4-fl uoro-benzvl)-3,8-diaza-bicvdo13 .2. l loct-8-vll-3-oxo- DroDenvl)-4-methoxv-N,N-dimethvl-benzenesulfonamide; a) 2-Bromo-5-chloro-4-methoxv-benzenesulfonvl chloride; 4-Bromo-1-chloro-2-methoxy-benzene (2 g; 9 mmol) is added dropwise under stirring at 0°C to chlorosulfonic acid (4.8 ml). The mixture is warmed to room temp. , poured on ice-water and extracted with TBME three times. The combined organic phases are dried over Na2S04, evaporated to dryness and the resulting solid washed with hexanes to deliver the title compound as colorless crystals (2.08 g; 72 %). 1 H-NMR (400MHz; DMSO-d6), 8 (ppm) : 2.78 (s, 6H) ; 3.97 (s, 3H) ; 7.60 (s, 1 H); 7.90 (s, 1 H). MS (m/z) ES+: 330 (MH+, 100).

References:

WO2005/103054,2005,A2 Location in patent:Page/Page column 56