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

HRID 1441458Notes

Reaction equation

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

Participants

Conditions

Temperature: -70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e2b3e1a73233488b812a9a73956f3ca0
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655654B2

Reaction notes

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