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

HRID 347158노트

반응식

HRID 347158 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8aa64023863b45f38ad9a999504c675a
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173043B2

반응 노트

불러오는 중…