Chloroprene → 4-Chloro-3,6-dihydrophthalic anhydride

HRID 1109824

Reaction equation

HRID 1109824 reaction equation
[CH2:1]=[CH:2][C:3]([Cl:5])=[CH2:4].Br[C:7]1[C:8]([O:10][C:11](=[O:13])[CH:12]=1)=[O:9]>>[Cl:5][C:3]1[CH2:4][C:12]2[C:11](=[O:13])[O:10][C:8](=[O:9])[C:7]=2[CH2:1][CH:2]=1

Participants

3

Reactant 2

HCID 31369ChloropreneHCID 80027Bromomaleic anhydride

Product 1

HCID 109869774-Chloro-3,6-dihydrophthalic anhydride

Conditions

Temperature
50 °C

Procedure

Chloroprene (13.6 g) and bromomaleic anhydride 14.6 g) were added together and the solution was heated to 50° C. for 11.5 hours. The reaction mixture was taken up in hot petroleum ether (bp 60° to 80° C.) and filtered. After cooling to room temperature, a solid was collected (6.2 g)- An additional 5 g of material remained in the mother liquors. The material consisted of a mixture of 4-chloro-3,6-dihydrophthalic anhydride, 4-chloro-l-bromo-1,2,3,6-tetrahydrophthalic anhydride and 4-chloro-2-bromo-1,2,3,6-tetrahydrophthalic anhydride.

Workup

  1. filtrationfiltered
  2. temperatureAfter cooling to room temperature
  3. customa solid was collected (6.2 g)- An additional 5 g of material
  4. additionThe material consisted of a mixture of 4-chloro-3,6-dihydrophthalic anhydride, 4-chloro-l-bromo-1,2,3,6-tetrahydrophthalic anhydride and 4-chloro-2-bromo-1,2,3,6-tetrahydrophthalic anhydride

Sources & evidence

ORD record
ord-2016bcdf934c4dff89ea01fa72006086
Source dataset
uspto-grants-1994_06
Patent number
US05322954

Linked notes

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