Ethyl Acetate → 6-Bromo-3,5-dimethylbenzo[d]isoxazole

HRID 874626Notes

Reaction equation

HRID 874626 reaction equation
C(O[N:5]=[C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([Br:15])=[CH:10][C:9]=1[OH:16])[CH3:7])(=O)C.CC(=O)OCC>C(Cl)Cl.CCCCCC>[Br:15][C:11]1[C:12]([CH3:14])=[CH:13][C:8]2[C:6]([CH3:7])=[N:5][O:16][C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 1363510592-(4-Bromo-2-hydroxy-5-methylphenyl)-1-azaprop-1-enyl acetate

Product 1

HCID 584870706-Bromo-3,5-dimethylbenzo[d]isoxazoleYield 23.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

Neat 2-(4-bromo-2-hydroxy-5-methylphenyl)-1-azaprop-1-enyl acetate (103) (0.5 g, 1.748 mmol) was heated at 175° C. for 2 h then at 100° C. for 1 h. After cooling down to r.t., the dark brown solid was dissolved in DCM and subjected to silica gel flash chromatography (0-40% B, A: hexane; B: 50% EA in hexane) to give 6-bromo-3,5-dimethylbenz[d]isoxazole (104) (92 mg, yield: 23.3%; purity>95%) as yellow crystals.

Sources & evidence

ORD record
ord-1596b8b40ae841f9b1efdc71f8e335f5
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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