2-(6-Bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione → 2-(6-Cyano-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione

HRID 732254Notes

Reaction equation

Br[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[C:6]([F:20])[C:5]([O:21][CH2:22][CH3:23])=[C:4]([O:24][CH2:25][CH3:26])[CH:3]=1.[Cu](C#N)[C:28]#[N:29]>CN(C)C=O>[C:28]([C:2]1[C:7]([CH2:8][N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])=[C:6]([F:20])[C:5]([O:21][CH2:22][CH3:23])=[C:4]([O:24][CH2:25][CH3:26])[CH:3]=1)#[N:29]

Participants

Conditions

Temperature: 155 °C

Procedure

A mixture of 2-(6-bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione (1.00 g, 2.37 mol), copper cyanide (0.42 g, 4.74 mol) and N,N-dimethylformamide (5 mL) was stirred at 155° C. for ten hours. After the reaction mixture was extracted with a 10% aqueous solution of ethylene diamine and toluene, the resultant organic layer was washed sequentially with a 10% aqueous solution of ethylene diamine and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off to give crude crystals, which were washed with ethyl acetate to give 0.52 g of the title compound (yield: 60%) as slightly green crystals.

Workup

extractionAfter the reaction mixture was extracted with a 10% aqueous solution of ethylene diamine and toluene
washthe resultant organic layer was washed sequentially with a 10% aqueous solution of ethylene diamine and saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtration
distillationthe solvent was distilled off
customto give crude crystals, which
washwere washed with ethyl acetate

Sources & evidence

ORD record: ord-7e1257a69b0b4a37b6ecd6f7715b72ca
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585982B2

Reaction notes

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