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Acetate → 2-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

HRID 745490
Notes
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Reaction equation

HRID 745490 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])[CH:11]=[CH2:12].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.CCOCC.O>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH:12]=[CH:11][CH2:10][N:13]1[C:17](=[O:18])[C:16]2[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]1=[O:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 175AcetateHCID 11776TriphenylphosphineHCID 684712-Bromo-m-xyleneHCID 224401N-Allylphthalimide

Product 1

HCID 544475222-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture 9.3 g (50 mmole) of 2-bromo-m-xylene, 15.0 g (80 mmole) of N-allylphthalimide, 0.56 (2.5 mmole) of paladium acetate and 1.44 (5.5 mmole) of triphenylphosphine were dissolved in 111 ml of triethylamine. The solution was placed in a sealed container and heated at 100° C. for 24 hours. The reaction was then diluted with 800 ml of ether and 200 ml of water. The aqueous layer was separated and the organic washed twice with 100 ml portions of 2N HCl. After filtering the organic phase, washing with saturated KHCO3 and brine, and drying over MgSO4, it was concentrated on the steam bath. The resulting solid product was purified by flash chromotography and used in subsequent reactions.

Workup

  1. customThe aqueous layer was separated
  2. washthe organic washed twice with 100 ml portions of 2N HCl
  3. filtrationAfter filtering the organic phase
  4. washwashing with saturated KHCO3 and brine
  5. dry with materialdrying over MgSO4, it
  6. concentrationwas concentrated on the steam bath
  7. customThe resulting solid product was purified by flash chromotography

Sources & evidence

ORD record
ord-57e64b5834e747359a4e6d2b2af52392
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04599325

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes