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

HRID 347158Notes

Reaction equation

HRID 347158 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8aa64023863b45f38ad9a999504c675a
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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