Bromine → 1-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

HRID 1359209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359209
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:28]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:28][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[O:13][C:14]3[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8]2

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827821-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

Produkt 1

HCID 181828161-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanoneAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Following the procedure described in Step 4 of Example 1, 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone (0.378 g, 1.05 mmol) was brominated using, bromine (0.08 mL, 1.6 mmol), and potassium acetate (1.02 g, 10.4 mmol), in glacial acetic acid (17 mL). Purification by flash chromatography (Biotage apparatus) using 15-20% chloroform in hexane as an eluant furnished the title compound as a dark brown gum (0.203 g). 1HNMR (300 MHz, DMSO-d6): δ10.95 (s, 1H), 8.35 (s, 1H), 8.2 (d, 1H, J=8.3 Hz), 8.0 (d, 1H, J=8.3 Hz), 7.95 (t, 2H, J=8.3 Hz), 7.85 (d, 1H, J=8.3 Hz), 7.35-7.55 (m, 3H), 2.65 (s, 2H), and 0.85 ppm (s, 9H).

Aufarbeitung

  1. customPurification by flash chromatography (Biotage apparatus)

Quellen und Nachweise

ORD-Eintrag
ord-43caa055ebf44eccbf6b49a55084559c
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599925B2

Notizen zur Reaktion

Wird geladen…