Bromoacetyl bromide → Oleyl bromoacetate
Reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([OH:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(C(C)C)CC)(C)C>O1CCCC1>[Br:1][CH2:2][C:3]([O:24][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of bromoacetyl bromide (0.49 ml; 5.65 mmol) in tetrahydrofuran (12 ml) is added, at 0° C., to a mixture of oleyl alcohol (1.00 ml; 3.77 mmol) and diisopropylethylamine (0.88 g; 5.65 mmol) in tetrahydrofuran (38 ml). The mixture is stirred for 2 h at 0° C. and then for 1 h at room temperature; it is then washed with 1N hydrochloric acid solution (20 ml) which is extracted with ether (50 ml). The combined organic phases are washed with saturated sodium carbonate solution (20 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography on a column of silica gel (eluent: 99/1 hexane/ether) to give oleyl 2-bromoacetate (1.31 g; 89%) in the form of a colorless oil.
Workup
- waitfor 1 h at room temperature
- washit is then washed with 1N hydrochloric acid solution (20 ml) which
- extractionis extracted with ether (50 ml)
- washThe combined organic phases are washed with saturated sodium carbonate solution (20 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- custompurified by chromatography on a column of silica gel (eluent: 99/1 hexane/ether)
Sources & evidence
- ORD record
- ord-0514c2e0f1024a2f80b5265d5df6ccfc
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291423B1
Reaction notes
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