Bromine → 1-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359208
[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:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:27]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:27][C:10]1[CH:11]=[C:2]([OH:1])[CH:3]=[C:4]2[C:9]=1[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827801-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

Produkt 1

HCID 181827891-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanoneAusbeute 58,6 %

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-methyl-1-butanone (0.863 g, 2.51 mmol) was brominated using bromine (0.15 mL, 2.9 mmol), and potassium acetate (2.45 g. 25.0 mmol) in glacial acetic acid (25 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant followed by chromatography on a Biotage apparatus using 15-20% chloroform in hexane as an eluant furnished 1-[2-(8-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone as an orange solid (0.623 g), mp 160-161° C. 1HNMR (200 MHz, DMSO-d6): δ10.95 (s,1H), 8.4 (s, 1H), 8.2 (d, 1H, J=8.6 Hz), 7.9-8.1 (m, 3H), 7.7-7.8 (d, 1H, J=6.8 Hz), 7.3-7.55 (m, 3H), 2.8 (d, 1H, J=6.8 Hz), 2.0-2.2 (m, 1H), and 0.75 ppm (d, 6H, J=6.3 Hz).

Aufarbeitung

  1. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d4b0469dba8b48f18bcd77aab09f22d1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599925B2

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