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

HRID 732253Notes

Reaction equation

HRID 732253 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]1[C:13]([F:33])=[C:14]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH3:32])[CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26])[CH3:10].CCCCCC>C(#N)C>[Br:1][C:27]1[C:14]([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])=[C:13]([F:33])[C:12]([O:11][CH2:9][CH3:10])=[C:29]([O:30][CH2:31][CH3:32])[CH:28]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 578383682-(3,4-Diethoxy-2-fluorobenzyl)isoindol-1,3-dione

Product 1

HCID 578383662-(6-Bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dioneYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (1.43 g, 8.07 mol) was added to a solution of 2-(3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione (2.52 g, 7.34 mol) in acetonitrile (30 mL) on ice. The mixture was stirred on ice for ten hours, and then at room temperature for six hours. The reaction mixture was extracted after the addition of a 5% aqueous solution of sodium thiosulfate and ethyl acetate; then the resultant organic layer was washed sequentially with 1N hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off and the residue was purified by silica gel column chromatography (diethyl ether, no-hexane) to give 1.12 g of the title compound (yield: 36%) as white crystals.

Workup

  1. extractionThe reaction mixture was extracted
  2. additionafter the addition of a 5% aqueous solution of sodium thiosulfate and ethyl acetate
  3. washthen the resultant organic layer was washed sequentially with 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (diethyl ether

Sources & evidence

ORD record
ord-333219e436f84d75a2af6eab105d83c1
Source dataset
uspto-grants-2009_09
Patent number
US07585982B2

Reaction notes

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