beta-Bromostyrene → 1,2,3,4,5-Pentafluoro-6-[(1Z)-2-phenylethenyl]benzene

HRID 1848950Notes

Reaction equation

[F:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([F:16])[C:5]([F:17])=[C:4]([F:18])[C:3]=1[F:19].FC1C(F)=C(F)C(F)=C(F)C=1.BrC=CC1C=CC=CC=1>>[F:1][C:2]1[C:7](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([F:16])[C:5]([F:17])=[C:4]([F:18])[C:3]=1[F:19]

Participants

Reactant 3

HCID 7667beta-Bromostyrene

HCID 9696Pentafluorobenzene

HCID 11231021HCID 11231021, compound

Product 1

HCID 247879971,2,3,4,5-Pentafluoro-6-[(1Z)-2-phenylethenyl]benzene

Procedure

FIG. 33 shows the resultant molecules (E)-1,2,3,4,5-pentafluoro-6-styrylbenzene and when the substrate is pentafluorobenzene and the haloalkene is beta-bromostyrene, and its 1H NMR spectrum. (Z)-1,2,3,4,5-Pentafluoro-6-styrylbenzene is also produced in this synthesis. The synthesis of (E)-1,2,3,4,5-pentafluoro-6-styrylbenzene and (Z)-1,2,3,4,5-pentafluoro-6-styrylbenzene is conducted using copper(I) iodide (19.1 mg, 0.1 mmol), beta-bromostyrene (183 mg, 1.0 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol), pentafluorobenzene (252 mg, 1.5 mmol), K3PO4 (424 mg, 2.0 mmol), and DMF/xylene (0.6 mL). After column chromatography (hexanes) and preparative HPLC (hexanes) 33 mg (12%) of an off-white solid ((Z)-1,2,3,4,5-pentafluoro-6-styrylbenzene) and 207 mg (77%) of a white solid ((E)-1,2,3,4,5-pentafluoro-6-styrylbenzene) are obtained. (E)-1,2,3,4,5-pentafluoro-6-styrylbenzene: 1H NMR (300 MHz, CDCl3) δ 6.98 (d, J=16.6 Hz, 1H), 7.30-7.48 (m, 4H), 7.50-7.56 (m, 2H). Data not shown for (Z)-1,2,3,4,5-pentafluoro-6-styrylbenzene.

Sources & evidence

ORD record: ord-5095882dc46049899dfb9749a8d8491b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952207B2

Reaction notes

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