3-BROMO-4-FLUOROBENZYLISOCYANIDE synthesis

Yield:728920-04-5 58%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine;trichlorophosphate in dichloromethane at 20; for 2.5 h;Cooling with ice;

Steps:

Synthesis of 2-; N-(3-bromo-4-fluorobenzyl)formamide (280 mg, 1.21 mmol), and N,N-diisopropylethylamine (702 mg, 5.43 mmol) were stirred in dichloromethane (10 ml) under ice-cooling. A solution of phosphorus oxychloride (278 mg, 1.81 mmol) in dichloromethane (5 ml) was added dropwise thereto. After the complete addition, the reaction mixture was stirred for 0.5 hour, and further stirred for 2 hours at room temperature. The reaction mixture was poured into dichloromethane, and then washed with water, an aqueous solution of sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. The residue was purified with silica gel column chromatography to obtain the desired compound (Solvent: hexane/ethyl acetate 95/5 and subsequently 90/10) in 150 mg and 58 % yield.'H-NMRCCDCls) δ: 4.61(2H, s), 7.13-7.58(3H, m)

References:

WO2012/4326,2012,A1 Location in patent:Page/Page column 56