4-Fluorostyrene → HCID 118656372, compound

HRID 926093Notes

Reaction equation

F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[CH2:26])=[CH:23][CH:22]=1>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:20][C:21]1[CH:28]=[CH:27][C:24](/[CH:25]=[CH:26]/[C:11]2[CH:12]=[CH:13][C:8]([S:7]([F:19])([F:18])([F:17])([F:16])[F:6])=[CH:9][CH:10]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1 (10.4 mg, 0.0315 mmol) in 0.4 mL of 95% aqueous ethanol was added dropwise to a solution of 4-fluorostyrene (9.8 mg, 0.080 mmol) and palladium(II) acetate (0.2 mg, 0.0009 mmol) in 0.10 g of 95% aqueous ethanol. The reaction mixture was heated on an oil bath at 70° C. for 5 h. After cooling, the mixture was filtered through a pad of Celite 545 and purified by SiO2 column chromatography (9:1 hexane/CH2Cl2) to give 2b (8.2 mg, 77% yield) as colorless crystals; m.p. 85.0-86.2° C. IR (ATR): {tilde over (v)}=1593, 1508, 1236, 1159, 1099, 964, 831, 818 cm−1. MS (GC, EI): m/z=324 [M+], 197 [M+ SF5], 177. 1H NMR (500 MHz, CDCl3): δ=7.73 (d, J=8.8 Hz, 2H), 7.55 (d, J=8.5 Hz, 2H), 7.51 (dd, J=8.8, 5.4 Hz, 2H), 7.15 (d, J=16.4 Hz, 1H), 7.08 (d, J=8.7 Hz, 2H), 7.01 (d, J=16.4 Hz, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=162.8 (C), 152.3 (C), 140.4 (C), 132.6 (C), 130.7 (CH), 128.4 (2CH), 126.3 (2CH), 126.2 (2CH), 126.2 (CH), 115.8 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.9 (quint, J=150.2 Hz, 1 F), 63.0 (d, J=150.2 Hz, 4 F), −112.7 (m, 1 F) ppm.

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through a pad of Celite 545
custompurified by SiO2 column chromatography (9:1 hexane/CH2Cl2)

Sources & evidence

ORD record: ord-9dcd97c8891d4350a61065ea7e1f545b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284336B1

Reaction notes

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