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

HRID 347158ノート

反応式

HRID 347158 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8aa64023863b45f38ad9a999504c675a
出典データセット
uspto-grants-2007_02
特許番号
US07173043B2

反応ノート

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