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

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]

Participants

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

customThe aqueous layer was separated
washthe organic washed twice with 100 ml portions of 2N HCl
filtrationAfter filtering the organic phase
washwashing with saturated KHCO3 and brine
dry with materialdrying over MgSO4, it
concentrationwas concentrated on the steam bath
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

Linked notes

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