Acetonitrile → 4-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(pentafluorosulfanyl)benzene (495.9 mg, 2.263 mmol) in CH2Cl2 (10 mL) was added dropwise to BF3.OEt2 (493.3 mg, 3.476 mmol) in a flask cooled with an ice-water bath. tert-Butyl nitrite (300.1 mg, 2.910 mmol) in 2 mL of CH2Cl2 was added dropwise and stirred at 0° C. for 1 h. The precipitated colorless crystals were isolated by filtration. The crystals was dissolve in CH3CN (0.4 mL) and precipitated by addition of ether to give pale yellow solid crystals, which were washed with diethyl ether. Removal of the solvent under vacuum afforded the title compound as pale yellow crystals (605.1 mg, 84%): IR (ATR): {tilde over (v)}=2924, 2852, 2309, 1574, 1418, 1304, 1053, 768 cm−1. 1H NMR (500 MHz, CD3CN): δ=8.72 (d, J=9.2 Hz, 2H), 8.40 (d, J=9.2 Hz, 2H) ppm. 13C NMR (125 MHz, CD3COCD3): δ=160.4, (C), 134.4 (2CH), 129.5 (2CH), 120.4 (C) ppm. 19F NMR (470 MHz, CD3CN): δ=77.7 (quint, J=151 Hz, 1 F), 60.9 (d, J=151 Hz, 4 F), −151.5 (s, 4 F) ppm.

Provenance & Evidence