3,4,5,6-Tetrahydrophthalic anhydride → 2-(4-Bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

HRID 1414369Notes

Reaction equation

HRID 1414369 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1>C(O)(=O)C>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([N:17]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])=[C:15]([F:20])[CH:14]=1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 1859322-(4-Bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10 parts of 3,4,5,6-tetrahydrophthalic anhydride in 100 parts of glacial acetic acid was treated in one portion with 11 parts of 4-bromo-2-fluoroaniline and was stirred for 30 minutes. The reaction mixture was refluxed for 16 hours and then poured over 200 parts ice. The resulting purple crystals were filtered and recrystallized from 100 parts methanol at -40°C to yield 13 parts of pink plates of 2-(4-bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione melting at 102.0°-102.5°C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. additionpoured over 200 parts ice
  3. filtrationThe resulting purple crystals were filtered
  4. customrecrystallized from 100 parts methanol at -40°C

Sources & evidence

ORD record
ord-b1048f93596a4d7d83b84e7c29be0cd7
Source dataset
uspto-grants-1977_01
Patent number
US04001272

Reaction notes

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