Triethylamine → 6-Bromo-2-naphthyl Trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

Triflic anhydride [(CF3SO2)2O, 1.8 ml, 3.03 g, 10.8 mmol] was added to a solution of 6-bromo-2-naphthol (2 g, 9.0 mmol) and triethylamine (NEt3) (1.52 ml, 1.09 g, 10.8 mmol) in dichloromethane (CH2Cl2) (40 ml) and under inert atmosphere at −10° C. After 2 h of stirring at −10° C., the reaction mixture was diluted in H2O (50 ml) and extractions with CH2Cl2 (3×40 ml) were carried out. The joined organic phases were washed with aq HCl (50 ml, 0.1 M), followed with H2O (50 ml) and were dried on Na2SO4. The filtration, evaporation and purification by column chromatography (SiO2, CH2Cl2) gave the title compound (3.25 g) as a colourless oil. IR (KBr) 3090, 1590, 1501, 1425, 1363, 1251, 1212, 1182, 1141, 1111, 1065, 960, 915, 882, 850, 801, 786, 767, 714, 653 y 609. M/Z (IQ, NH3) 356 [M+(81Br), 53%], 354 [M+ (79Br), 63], 223 [M-SO2CF3+ (81Br), 63] y 221 [M-SO2CF3+ (79Br), 100].

Provenance & Evidence