Hydrogen Bromide → 3-(4-Fluoro-phenyl)-benzo[b]thiophen-6-ol

HRID 347158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347158
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1.Br.[OH-].[Na+]>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 110106623-(4-Fluorophenyl)-6-methoxybenzo[b]thiophene

Produkt 1

HCID 223141963-(4-Fluoro-phenyl)-benzo[b]thiophen-6-olAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

29.96 g 3-(4-Fluoro-phenyl)-6-methoxy-benzo[b]thiophene in 230 ml acetic acid were treated with 130 ml (62% aq) HBr at 125° C. for 4 h. The solution was added slowly to a cooled solution of 210 g NaOH in 600 ml water, the pH was adjusted to 8–9, and the inorganic phase was extracted with EtOAc. The combined organic phases were washed with brine and dried with Na2SO4. Column chromatography on silica gel with hexane: EtOAc 4.1 yielded 20.0 g (73%) 3-(4-Fluoro-phenyl)-benzo[b]thiophen-6-ol as light brown solid, MS: 244 (M).

Aufarbeitung

  1. extractionthe inorganic phase was extracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-8aa64023863b45f38ad9a999504c675a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173043B2

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