1,2-Dibromoethane → 1,4-Dibromo-2-(2-bromoethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br>[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[O:9][CH2:12][CH2:11][Br:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2,5-dibromophenol (134) (1.26 g, 5 mmol) and 1,2-dibromoethane (135) (431 μl, 5 mmol) in 5 ml 1N NaOH was stirred at 80° C. for 40 h. After cooling down, the reaction mixture was extracted with diethyl ether. Org. phase was washed with 1 N NaOH and brine subsequently. Org. phase was dried over sodium sulfate concentrated to give 922 mg (yield 51%, purity ca 90%) 1,4-dibromo-2-(2-bromoethoxy)benzene (136) as orange-red oil which was used directly for further reaction without purification.
Workup
- temperatureAfter cooling down
- extractionthe reaction mixture was extracted with diethyl ether
- washphase was washed with 1 N NaOH and brine subsequently
- dry with materialphase was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8f2c50bb3f874bdb85ad6f5f69a3578f
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546403B2
Reaction notes
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