2-(4-Bromophenyl)ethanol → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

HRID 2383368Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:20]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][N:22]2[C:23](=[O:32])[C:24]3[C:25](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:27])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-(4-bromophenyl)ethanol (48.3 g) in acetonitrile (480 mL) was added diisopropylethylamine (46.6 g), N-vinylphthalimide (43.7 g) and tri-o-tolylphosphine (7.31 g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7 g) was added and the mixture was stirred at 90° C. for 21 hr under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24 g.

Workup

customthe mixture was purged with nitrogen gas three times
additionPalladium acetate (2.7 g) was added
temperatureThe reaction was cooled
filtrationthe precipitated product collected by filtration
dissolutionThe resulting solid was re-dissolved in dichloromethane
filtrationethyl acetate and filtered through silica gel
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-18504441bd204a2089c41bc9ea38e454
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263623B2

Reaction notes

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