Acetic Acid → Methyl 2-[6-hydroxy-4-(trifluoromethyl)benzo[b]thiophen-3-yl]acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:9]2[C:10]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:12]([O:14]C)=[CH:13][C:8]=2[S:7][CH:6]=1.CC(O)=O.Br>[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:9]2[C:10]([C:16]([F:19])([F:17])[F:18])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1Participants
Conditions
- Temperature
- 130 °C
Procedure
To a mixture of methyl(6-methoxy-4-(trifluoromethyl)-1-benzothiophen-3-yl)acetate obtained above (405 mg) and AcOH (1.5 mL) was added 48% hydrobromic acid (3 mL) at room temperature. The mixture was stirred at 130° C. for 40 min under microwave irradiation. The mixture was poured into brine at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. A mixture of the residue, MeOH and conc. H2SO4 (0.071 mL) was refluxed for 1 h. The mixture was poured into brine at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine twice, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (232 mg).
Workup
- extractionextracted with EtOAc
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- additionA mixture of the residue, MeOH and conc. H2SO4 (0.071 mL)
- temperaturewas refluxed for 1 h
- additionThe mixture was poured into brine at room temperature
- extractionextracted with EtOAc
- customThe organic layer was separated
- washwashed with brine twice
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
Sources & evidence
- ORD record
- ord-03b42150b72e46f9888fe788df691f56
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238639B2
Reaction notes
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