Ethanol → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid ethyl ester

HRID 1183278Notes

Reaction equation

HRID 1183278 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:22][CH2:23]O>>[CH2:22]([O:16][C:15](=[O:17])[CH2:14][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:23]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 66577233[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid

Product 1

HCID 66577263[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid ethyl ester

Procedure

To [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid (0.200 g, 0.68 mmol) in EtOH (3 mL) was added thionyl chloride (0.10 mL, 1.35 mmol), and the reaction was stirred for 1 hour. The mixture was quenched with saturated aqueous NH4Cl and diluted with EtOAc and H2O. After standard aqueous workup, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customThe mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc and H2O
  3. customAfter standard aqueous workup, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b1b06ae8784e4e26b2c0e5da6b776395
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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