Potassium Carbonate → 2-Bromo-1-methoxy-4-(2-methoxy-ethoxy)-benzene
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[CH:14]=[C:15]([OH:21])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:21][CH2:4][CH2:3][O:2][CH3:1])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-bromoethyl methyl ether (0.07 mL, 0.74 mmol) was added to a mixture of potassium carbonate (136 mg, 0.99 mmol) and 3-bromo-4-methoxy-phenol (100 mg, 0.49 mmol) in DMF (2 mL) and mix heated at 100° C. for 1 hr. Reaction mixture was allowed to cool and partitioned between ethyl acetate (20 mL×2) and water (20 mL). The combined organic phases were washed with sat. aqueous sodium chloride solution (40 mL) and dried over sodium sulphate. Solvents were removed in vacuo to afford a crude oil which was purified by flash chromatography on silica gel, eluting with a gradient of 0-10% ethyl acetate in hexane to afford the title compound (113 mg, 88%) as a colourless liquid.
Workup
- additionmix
- customReaction mixture
- temperatureto cool
- custompartitioned between ethyl acetate (20 mL×2) and water (20 mL)
- washThe combined organic phases were washed with sat. aqueous sodium chloride solution (40 mL)
- dry with materialdried over sodium sulphate
- customSolvents were removed in vacuo
- customto afford a crude oil which
- customwas purified by flash chromatography on silica gel
- washeluting with a gradient of 0-10% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-252b91457904416e80633f727d9a2667
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450346B2
Reaction notes
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