Pentafluorobenzyl bromide → HCID 88371353, Verbindung

HRID 440161

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[F:12][C:13]1[C:18]([CH2:19]Br)=[C:17]([F:21])[C:16]([F:22])=[C:15]([F:23])[C:14]=1[F:24]>>[F:12][C:13]1[C:18]([CH2:19][O:1][C:2]2[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([O:8][CH2:19][C:18]3[C:17]([F:21])=[C:16]([F:22])[C:15]([F:23])=[C:14]([F:24])[C:13]=3[F:12])[CH:7]=2)=[C:17]([F:21])[C:16]([F:22])=[C:15]([F:23])[C:14]=1[F:24]

Komponenten

Edukt 2

HCID 74484Pentafluorobenzyl bromide

HCID 1039933',5'-Dihydroxyacetophenone

Produkt 1

HCID 88371353HCID 88371353, VerbindungAusbeute 98 %

Versuchsvorschrift

Synthesized by 1:2 ratio of 3',5'-dihydroxyacetophenone to pentafluorobenzyl bromide. Yield: 98%. m.p. 102°-103° C. 1H NMR, δ: 2.60 (s, 3H, CH3CO), 5.22 (s, 4H, CH2O), 6.83 (bs, 1H, H-C4'), 7.24 (d, 2H, J=1.8 Hz, H-C2' & H-C6') ppm; 13C NMR, δ: 26.0 (CH3CO), 57.4 (CH2O), 106.4 (C4'), 107.4 (C2' & C6'), 109.7 (C1", 2JC-F =17 Hz) 137.4 (C2" & C6", JC-F =249 Hz), 139.2 (C1'), 141.7 (C4", JC-F =256 Hz), 145.7 (C3" & C5", JC-F =251 Hz), 159.2 (C3' & C5'), 196.7 (C=O) ppm. MS (EI): 331 ([M-PFBz]+); MS (ECNI): 331 ([M-PFBz]-, 100%).

Quellen und Nachweise

ORD-Eintrag: ord-855b77e8c7314295a9fbd30cb6ae6ac8
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05516931

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