Hydrogen Bromide → 2-(4-Octylphenyl)ethyl bromide
Reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O-]S([O-])=O.[Na+].[Na+].[BrH:24]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][Br:24])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
2-(4-octylphenyl)ethanol (5) (46.9 g) is added within 10 min to an aqueous solution containing 3.05 g Na2SO3, 252.9 g 48% HBr and 3.2 g tricaprylmethylammonium chloride. The reaction mixture is heated to 100° C. for 18 to 22 hours with stirring. The resulting 2-phase mixture is cooled to room temperature, diluted with toluene (150 ml) and the aqueous phase is then removed. The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution. The organic phase is treated with basic aluminium oxide, then filtered. The filter residue is washed with toluene (50 ml) and evaporated to yield compound (19) as a clear pale yellow oil. The resulting Compound (19) has the same physico-chemical characteristics as indicated in Example 14.
Workup
- temperatureThe resulting 2-phase mixture is cooled to room temperature
- customthe aqueous phase is then removed
- washThe organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution
- additionThe organic phase is treated with basic aluminium oxide
- filtrationfiltered
- washThe filter residue is washed with toluene (50 ml)
- customevaporated
Sources & evidence
- ORD record
- ord-e20e5047779d46679bd811bffa8c7949
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605744B2
Reaction notes
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