Triethylamine → 6-Bromo-2-naphthyl Trifluoromethanesulfonate

HRID 1991919Notes

Reaction equation

[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22](O)[CH:21]=[CH:20]2.C(N(CC)CC)C>ClCCl.O>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([Br:16])[CH:18]=2)[CH:23]=1)(=[O:3])=[O:2]

Participants

Conditions

Temperature: -10 °C

Procedure

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].

Workup

extractionextractions with CH2Cl2 (3×40 ml)
washThe joined organic phases were washed with aq HCl (50 ml, 0.1 M)
customwere dried on Na2SO4
filtrationThe filtration, evaporation and purification by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record: ord-eead8ad5b3564752a35b9edb999b542e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645910B2

Reaction notes

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