2-Butene, 1,4-dibromo- → HCID 54196002, compound

HRID 1658435Notes

Reaction equation

HRID 1658435 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

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

  1. customThe mixture is extensively freed from dimethylformamide on a rotary evaporator
  2. customthe residue is partitioned between water and methylene chloride
  3. dry with materialThe methylene chloride phase is dried over calcium chloride
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe residue is distilled under a water-jet vacuum, whereby the fractions
  7. 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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