3-bromo-4-(methylsulfanyl)benzaldehyde synthesis

Yield:694481-10-2 44%

Reaction Conditions:

with potassium carbonate in 1-methyl-pyrrolidin-2-one at 70; for 7 h;Heating / reflux;

Steps:

22.a Example 22 N-[3-Bromo-4-(methylsulfonyl)benzyl]-6-methyl-2-oxo-1-[3- (TRIFLUOROMETHEL) PHENYLL-1. 2-DIHYDROPERIDINE-3-CARBOXAMIDE; a) 3-BROMO-4- (METHYLTHIO) BENZALDEHYDE

To a solution of 3-bromo-4-fluorobenzaldehyde (0.5 g, 2.5 mmol) in NMP (10 ml), potassium carbonate (0.68 g, 4.92 mmol) and sodium metanethiolate (0.26 g, 3.69 mmol) were added. The mixture was heated to 70 °C for 7 h, cooled, and partitioned between EtOAc and water. The organic phase was dried, filtered, evaporated and purified by column chromatography on silica using heptane/EtOAc (4: 1) as eluent to afford the title compound (0.25 g, 44%). 1H-NMR (CDCl3) : 6 9.89 (1H, s); 8.00 (1H, d); 7.79 (1H, dd); 7.23 (1H, d); 2.54 (3H, s). APCI-MS M/Z : 465. 3 [MH]

References:

WO2004/43924,2004,A1 Location in patent:Page 128