1-Ethenyl-4-methylbenzene → (E)-4-Methyl-4'-(pentafluorosulfanyl)stilbene

HRID 591364Notes

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.[CH3:20][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>[CH3:20][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 (10.0 mg, 0.0315 mmol) in 0.4 mL of 95% aqueous ethanol was added dropwise to a solution of 4-methylstyrene (9.0 mg, 0.076 mmol) and palladium(II) acetate (0.2 mg, 0.0009 mmol) in 0.12 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 2c (8.3 mg, 82% yield) as colorless crystals; m.p. 165.2-166.5° C. IR (ATR): {tilde over (v)}=1593, 1514, 1450, 1416, 1329, 1265, 1098, 972, 962, 841 cm−1. MS (GC, EI): m/z=320 [M+], 193 [M+-F5S], 178 [M+-CH3F5S]. 1H NMR (500 MHz, CDCl3): δ=7.72 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.16 (d, J=16.4 Hz, 1H), 7.04 (d, J=16.4 Hz, 1H), 2.38 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=152.3 (C), 140.8 (C), 138.6 (C), 133.6 (C), 131.9 (CH), 129.5 (2CH), 126.7 (2CH), 126.3 (2CH), 126.2 (2CH), 125.3 (CH), 21.3 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=85.1 (quint, J=150 Hz, 1 F), 63.1 (d, J=150 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-ef5596a308314dff947cad5884973865
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238660B1

Reaction notes

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