Benzyl Bromide → 1-(Benzyloxy)-2,5-dibromo-4-(dodecyloxy)benzene
Reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:13]([Br:29])=[CH:12][C:11]=1[OH:30].C([O-])([O-])=O.[K+].[K+]>C(O)C>[Br:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:13]([Br:29])=[CH:12][C:11]=1[O:30][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Benzyl bromide (3.8 ml, 0.031 mol) was added drop wise to a stirred solution of 2,5-dibromo-4-dodecyloxy phenol (a) (6.95 g, 0.015 mol) and anhydrous K2CO3 (3.28 g, 0.023 mol) in 700 ml of absolute ethanol at 40-50° C. The reaction mixture was stirred for 10 h at 50° C., progress of the reaction was monitored using TLC, cooled to RT and evaporated to remove the solvent. An equal volume of distilled water was added to the residue and the mixture was stirred for one hour at 0° C. The resulting precipitate was collected by filtration, washed with water, and dried in vacuum. Recrystallization was done in methanol to get 80% yield.
Workup
- temperaturecooled to RT
- customevaporated
- customto remove the solvent
- additionAn equal volume of distilled water was added to the residue
- stirringthe mixture was stirred for one hour at 0° C
- filtrationThe resulting precipitate was collected by filtration
- washwashed with water
- customdried in vacuum
- customRecrystallization
- customto get 80% yield
Sources & evidence
- ORD record
- ord-df43d9c23ddd48e58fff5fa5dd126afd
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700040B2
Reaction notes
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