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

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

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-methylbenzamide (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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-7bfe84fd85094276ad6be475386f2c07
Quelldatensatz: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07511138B2

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