Styrene → HCID 102367693, compound

HRID 926091Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

EtOH as Solvent: A solution of 1 (10.0 mg, 0.0315 mmol) in 0.4 mL of 95% aqueous ethanol was added dropwise to a solution of styrene (6.5 mg, 0.062 mmol) and palladium(II) acetate (0.5 mg, 0.002 mmol) in 0.11 g of 95% aqueous ethanol. The reaction mixture was heated by an oil bath at 70° C. for 15 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 2a (7.4 mg, 77% yield) as colorless crystals; m.p. 121.6-122.0° C. IR (ATR): {tilde over (v)}=3028, 1593, 1499, 1450, 1096, 964 cm−1. MS (GC, EI): m/z=306 [M+], 179. 1H NMR (500 MHz, CDCl3): δ=7.73 (d, J=8.5 Hz, 2H), 7.56 (d, J=8.5 Hz, 2H), 7.53 (d, J=7.4 Hz, 2H), 7.39 (t, J=7.4 Hz, 2H), 7.31 (t, J=7.4 Hz, 1H), 7.19 (d, J=16.4 Hz, 1H), 7.09 (d, J=16.4 Hz, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=152.5 (C), 140.6 (C), 136.4 (C), 132.0 (CH), 128.8 (2CH), 128.5 (CH), 126.8 (2CH), 126.3 (5CH) ppm. 19F NMR (470 MHz, CDCl3): δ=89.9 (quint, J=150.2 Hz, 1 F), 61.0 (d, J=150.2 Hz, 4 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-7cd72a2d171742e4b46bd3238dec98bd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284336B1

Reaction notes

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