Water → 7-Chloro-3-(4-ethoxy-2-fluorophenyl)-6-methoxy-1,2-benzisoxazole

HRID 652952Notes

Reaction equation

HRID 652952 reaction equation
Cl[C:2]1[C:20]([Cl:21])=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][C:3]=1/[C:4](=[N:15]\[OH:16])/[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:6]=1[F:14].[H-].[Na+].O.C(OCC)C.CC(=O)CC>CN(C)C=O>[Cl:21][C:20]1[C:2]2[O:16][N:15]=[C:4]([C:5]3[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][C:6]=3[F:14])[C:3]=2[CH:17]=[CH:18][C:19]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13015701(NZ)-N-[(2,3-dichloro-4-methoxyphenyl)-(4-ethoxy-2-fluorophenyl)methylidene]hydroxylamineHCID 19800284Diethyl ether 2-butanone

Product 1

HCID 130157027-Chloro-3-(4-ethoxy-2-fluorophenyl)-6-methoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 23.3 g of Z-2,3-dichloro-4'-ethoxy-2'-fluoro-4-methoxybenzophenone oxime in 175 ml dimethylformamide is added to 1.85 g of sodium hydride in 35 ml of dimethylformamide. After stirring 30 min at room temperature, the reaction is worked up with water and 1:1 diethyl ether/2-butanone. Concentration of the dried organic phase, trituration of the product with hexane and recrystallization from toluene/hexane gives 7-chloro-3-(4-ethoxy-2-fluorophenyl)-6-methoxy-1,2-benzisoxazole, mp 151°-152° C.

Workup

  1. customConcentration of the dried organic phase, trituration of the product with hexane and recrystallization from toluene/hexane

Sources & evidence

ORD record
ord-2c9e6838e1a544799c2a3e3da77b71e3
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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