Triethylamine → Bis(allyloxycarbonylmethyl) tetrabromoterephthalate

HRID 1248257Notes

Reaction equation

HRID 1248257 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([Br:11])[C:5]([Br:12])=[C:4]([C:13]([OH:15])=[O:14])[C:3]=1[Br:16].Cl[CH2:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20].C(N([CH2:30][CH3:31])CC)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([C:8]([O:10][CH2:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[O:9])=[C:6]([Br:11])[C:5]([Br:12])=[C:4]([C:13]([O:15][CH2:18][C:19]([O:21][CH2:22][CH:30]=[CH2:31])=[O:20])=[O:14])[C:3]=1[Br:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76206Allyl chloroacetateHCID 224162Tetrabromoterephthalic Acid

Product 1

HCID 54532742Bis(allyloxycarbonylmethyl) tetrabromoterephthalate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a liquid mixture consisting of 24 parts of tetrabromoterephthalic acid and 60 parts of chloroform, were dropped with stirring 20 parts of allyl chloroacetate. Thereafter, 13 parts of triethylamine were added dropwise while cooling the resulting mixture at 15°-20° C. The mixture was heated until chloroform started to reflux. At the same temperature, the mixture was maintained for 8 hours. After allowing the liquid reaction mixture to cool, it was poured in a separation funnel and washed first with dilute hydrochloric acid and then with water. The organic layer was concentrated under reduced pressures and the resulting white solid was recrystallized from ethyl acetate, thereby obtaining 25 parts of bis(allyloxycarbonylmethyl) tetrabromoterephthalate (hereinafter called "Compound E") as white irregular crystals. (m.p. 146°-148° C.).

Workup

  1. additionwere dropped
  2. temperaturewhile cooling the resulting mixture at 15°-20° C
  3. temperatureto reflux
  4. temperatureAt the same temperature, the mixture was maintained for 8 hours
  5. customthe liquid reaction mixture
  6. temperatureto cool
  7. additionit was poured in a separation funnel
  8. washwashed first with dilute hydrochloric acid
  9. concentrationThe organic layer was concentrated under reduced pressures
  10. customthe resulting white solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e64a6339c34e4bd09301f41f64549772
Source dataset
uspto-grants-1985_06
Patent number
US04522993

Reaction notes

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