trans-1,4-Dibromo-2-butene → 2-(4-Bromobut-2-en-1-yl)isoindoline-1,3-dione

HRID 1449648Notes

Reaction equation

HRID 1449648 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Br:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17]Br>CC(C)=O>[C:1]1(=[O:11])[N:5]([CH2:17]/[CH:16]=[CH:15]/[CH2:14][Br:13])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 641245trans-1,4-Dibromo-2-buteneHCID 24194345Phthalimide potassium salt

Product 1

HCID 105168412-(4-Bromobut-2-en-1-yl)isoindoline-1,3-dioneYield 56.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
85 °C

Procedure

Potassium phthalimide (18.5 g, 0.1 mol) was added in portions over 5 h to a stirred solution of (E)-1,4-dibromobut-2-ene (21.4 g, 0.1 mol) in acetone (200 ml) at 85° C. The suspension was stirred for 24 h at 85° C., then cooled and filtered. The filtrate was concentrated in vacuo to afford a white solid, which was recrystallised three times from acetone to yield (E)-1-phthalimido-4-bromobut-2-ene (15.76 g, 56.2%). δH (90 MHz, CDCl3) 3.88 (2H, d), 4.28 (2H, d), 5.92 (2H, m) and 7.80 (4H, m).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a white solid, which
  5. customwas recrystallised three times from acetone

Sources & evidence

ORD record
ord-3a66998adbbc4d708dc110306827a6f4
Source dataset
uspto-grants-1997_02
Patent number
US05599847

Reaction notes

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