5-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazole → [3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone

HRID 1441458ノート

反応式

HRID 1441458 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:17]=1)=[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[O:8][N:9]=2.[Li]CCCC.CON(C)[C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>C1COCC1>[Cl:16][C:12]1[CH:11]=[C:10]([C:7]2[O:8][N:9]=[C:5]3[CH:4]=[CH:3][C:2]([C:26]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:35])=[CH:17][C:6]=23)[CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 120166705-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazoleHCID 15105748N,4-Dimethoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 17976096[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.13 m) was added at −70° C. to THF (300 ml ) under N2 flow. A solution of BuLi (0.143 mol) was added dropwise. The mixture was stirred at −70° C. for 10 minutes. A solution of N,4-dimethoxy-N-methyl-benzamide (0.117 mol) in THF (100 ml) was added dropwise at −70° C. The mixture was stirred at −70° C. for 1 hour, poured out on ice/EtOAc and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried under a vacuo, yielding 19.5 g (41%) of [3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)- methanone (intermediate 10).

後処理

  1. stirringThe mixture was stirred at −70° C. for 1 hour
  2. additionpoured out on ice/EtOAc
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from diethyl ether
  9. filtrationThe precipitate was filtered off
  10. customdried under a vacuo

出典と根拠

ORDレコード
ord-e2b3e1a73233488b812a9a73956f3ca0
出典データセット
uspto-grants-2010_02
特許番号
US07655654B2

反応ノート

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