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

HRID 732253ノート

反応式

HRID 732253 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-333219e436f84d75a2af6eab105d83c1
出典データセット
uspto-grants-2009_09
特許番号
US07585982B2

反応ノート

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