Acetonitrile → 4-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

HRID 926090Notes

Reaction equation

[F:1][S:2]([F:12])([F:11])([F:10])([F:9])[C:3]1[CH:8]=[CH:7]C=C[CH:4]=1.[B:13]([F:16])([F:15])[F:14].CCOCC.[N:22](OC(C)(C)C)=O.[CH3:29][C:30]#[N:31]>C(Cl)Cl>[F:14][B-:13]([F:1])([F:16])[F:15].[F:1][S:2]([F:12])([F:11])([F:10])([F:9])[C:3]1[CH:8]=[CH:7][C:30]([N+:31]#[N:22])=[CH:29][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperaturecooled with an ice-water bath
customThe precipitated colorless crystals were isolated by filtration
customprecipitated by addition of ether
customto give pale yellow solid crystals, which
washwere washed with diethyl ether
customRemoval of the solvent under vacuum

Sources & evidence

ORD record: ord-922e13e610ea45fd8e23be42b1750b53
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284336B1

Reaction notes

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