Cesium carbonate → 4-Bromo-2-methoxy-1-(2-methoxyethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:11]([O-])([O-])=O.[Cs+].[Cs+].BrC[CH2:19][O:20][CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:19][O:20][CH3:21])=[C:4]([O:10][CH3:11])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2.0 g (9.65 mmol) 4-bromoguaiacol and 1.89 g (5.8 mmol) Cs2CO3 are suspended in 20.0 ml dry DMF and 1.02 ml (10.6 mmol) 2-bromoethylmethylether are introduced at RT under an argon flux. The resulting pale brown suspension is heated to 100° C. for 15 h. After cooling, the reaction mixture is partitioned between EtOAc and water. The aqueous phase is re-extracted twice with EtOAc. The combined organic solution is washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound as a light yellow residue.
Workup
- temperatureAfter cooling
- customthe reaction mixture is partitioned between EtOAc and water
- extractionThe aqueous phase is re-extracted twice with EtOAc
- washThe combined organic solution is washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3eac43541f294ec7a007f459bd4252be
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193189B2
Reaction notes
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