4-Iodo-3,5-dimethyl-1,2-oxazole → 4-m-Bromophenyl-3,5-dimethylisoxazole

HRID 653624Notes

Reaction equation

HRID 653624 reaction equation
[CH3:1][C:2]1[C:6](I)=[C:5]([CH3:8])[O:4][N:3]=1.[Br:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.BrC1C=C(C2C=NC=CC=2)C=CC=1>>[Br:9][C:10]1[CH:15]=[C:14]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:8])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 6138834-Iodo-3,5-dimethyl-1,2-oxazoleHCID 2734318(3-Bromophenyl)boronic acidHCID 131504013-(3-Bromophenyl)pyridine

Product 1

HCID 198894224-m-Bromophenyl-3,5-dimethylisoxazoleYield 119%

Procedure

The reaction of 3,5-dimethyl-4-iodoisoxazole (Kochetkov, N. K. Zhurnal Obschchie Khimii, 31, 2167-2172 (1961)) (2.4 g, 11 mmol) with 3-bromophenylboronic acid (2.24 g, 11 mmol) using the procedure for the preparation of 3-(3'-bromophenyl)pyridine gave 3.3 g crude 4-m-bromophenyl-3,5-dimethylisoxazole. After a quick filtration on Si gel (eluting with CH2Cl2), the material was further purified by preparative TLC on 12-1000μ Si Gel GF plates (eluting with 10% acetone/hexane and extracting with 10% MeOH/CH2Cl2), to provide 1.2 g of the arylated isoxazole. Sublimation (ambient to 70° C., high vacuum) of 0.5 g provided 404 mg of analytically pure material.

Sources & evidence

ORD record
ord-26ec679f90ee4ca59b80fedce56949d2
Source dataset
uspto-grants-1992_07
Patent number
US05128335

Reaction notes

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