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

HRID 270387ノート

反応式

HRID 270387 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-e6459a74037a475d9621c5ed4836e490
出典データセット
uspto-grants-2008_11
特許番号
US07449483B2

反応ノート

読み込み中…