1-Bromo-3-(2,2-diethoxyethoxy)benzene → 6-Bromo-1-benzofuran
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH:10](OCC)OCC)[CH:3]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:10]=[CH:9][O:8][C:4]=2[CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of the acetal 15-2 in toluene (200 mL) was added polyphosphoric acid (20 g). The biphasic mixture was heated to 100° C. and stirred at this temperature for 4 h. The mixture was cooled to room temperature, poured onto ice, and extracted with Et2O (2×200 mL). The combined organic extracts were washed with saturated aq NaHCO3 and brine. The solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (100% hexanes) to give the product 15-3 as a yellow oil.
Workup
- temperatureThe mixture was cooled to room temperature
- additionpoured onto ice
- extractionextracted with Et2O (2×200 mL)
- washThe combined organic extracts were washed with saturated aq NaHCO3 and brine
- dry with materialThe solution was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (100% hexanes)
Sources & evidence
- ORD record
- ord-d91a457291414103a95ad2230eeac512
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211184B1
Reaction notes
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