Hexahydrophthalic anhydride → 2-(4-Bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

HRID 1288039Notes

Reaction equation

HRID 1288039 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH:10]12[C:19](=O)[O:18][C:16](=[O:17])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2>C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:16](=[O:17])[CH:11]3[CH:10]([CH2:15][CH2:14][CH2:13][CH2:12]3)[C:19]2=[O:18])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 85689Hexahydrophthalic anhydrideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 129065652-(4-Bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

11.4 Parts of 4-bromo-2-fluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid and the mixture was stirred for 2 hours. The mixture was refluxed for 20 hours and then poured into 200 parts of ice. The resulting purple crystals were filtered and recrystallized from 70 parts of methanol at -40° C to yield 7.6 parts of lavender crystals of 2-(4-bromo-2-fluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 90°-92° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. additionpoured into 200 parts of ice
  3. filtrationThe resulting purple crystals were filtered
  4. customrecrystallized from 70 parts of methanol at -40° C

Sources & evidence

ORD record
ord-92b527d061294c4e9df39d02d50d11d5
Source dataset
uspto-grants-1976_10
Patent number
US03987057

Reaction notes

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