2-Butene, 1,4-dibromo- → HCID 54196002, compound
Reaction equation
[Br:1][CH2:2][CH:3]=[CH:4][CH2:5]Br.[C:7]([O-:10])(=[O:9])[CH3:8].[Na+]>CN(C)C=O>[C:7]([O:10][CH2:5][CH:4]=[CH:3][CH2:2][Br:1])(=[O:9])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
93 g of 1,4-dibromobut-2-ene are treated in 250 ml of dimethylformamide with 35.5 g of anhydrous sodium acetate and stirred for 1 hour at 100°C. The mixture is extensively freed from dimethylformamide on a rotary evaporator and the residue is partitioned between water and methylene chloride. The methylene chloride phase is dried over calcium chloride, filtered and concentrated. The residue is distilled under a water-jet vacuum, whereby the fractions are collected between 95° and 105°C at 10-15 mm; nD25 =1.502. There is obtained 1-acetoxy-4-bromobut-2-ene as a colourless liquid.
Workup
- customThe mixture is extensively freed from dimethylformamide on a rotary evaporator
- customthe residue is partitioned between water and methylene chloride
- dry with materialThe methylene chloride phase is dried over calcium chloride
- filtrationfiltered
- concentrationconcentrated
- distillationThe residue is distilled under a water-jet vacuum, whereby the fractions
- customare collected between 95° and 105°C at 10-15 mm
Sources & evidence
- ORD record
- ord-8ff3adfdd76a44619c366bf142486e45
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03963777
Reaction notes
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