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

HRID 1624381Notes

Reaction equation

HRID 1624381 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-5732b34752e142c7b69d910cd67d8808
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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