1,2-Dibromoethane → HCID 23001076, compound
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.[OH-].[Na+]>>[Br:10][CH2:11][CH2:12][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]Participants
4
Procedure
To a mixture of 2,3-dichlorophenol (20 g, 0.123 mol) and 1,2-dibromoethane (30.5 g, 0.162 mol) was added a sodium hydroxide solution (5 g, 0.125 mol in 125 ml of water), and the mixture was heated under reflux for 8 h. The mixture was allowed to cool and extracted with chloroform (2×100 ml). The combined extracts were washed with 1N aqueous sodium hydroxide solution (100 ml), dried, filtered and concentrated in vacuo. The residue was distilled at 106° C./0.3 mm of mercury to afford on cooling to room temperature the title compound as a yellow solid (20 g, 60%).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 8 h
- temperatureto cool
- extractionextracted with chloroform (2×100 ml)
- washThe combined extracts were washed with 1N aqueous sodium hydroxide solution (100 ml)
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuo
- distillationThe residue was distilled at 106° C./0.3 mm of mercury
- customto afford
Sources & evidence
- ORD record
- ord-bf8d6b94b8af4fa1bd27fefdc835f10c
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610711B2
Reaction notes
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