Ammonium Chloride → 1-(3-Bromo-5-isoxazolyl)-1-propanone

HRID 559716Notes

Reaction equation

HRID 559716 reaction equation
CON(C)[C:4]([C:6]1[O:10][N:9]=[C:8]([Br:11])[CH:7]=1)=[O:5].[CH2:13]([Mg]Br)[CH3:14].[NH4+].[Cl-]>C1COCC1>[Br:11][C:8]1[CH:7]=[C:6]([C:4](=[O:5])[CH2:13][CH3:14])[O:10][N:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59278382HCID 59278382, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 138021011-(3-Bromo-5-isoxazolyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of 3-bromo-isoxazole-5-carboxylic acid methoxy-methyl-amide (1.20 g, 5.11 mmol) in THF (56 mL) was added a 1 M solution of ethylmagnesium bromide (13.0 mL, 13.0 mmol) in THF dropwise over a 5 minutes period. The reaction was monitored by TLC (hexanes-EtOAc 4:1). After 5 hours, the reaction was transferred via a 16 gauge cannula to a 0° C. solution of saturated aqueous NH4Cl (75 mL). The resultant heterogeneous mixture was warmed to room temperature and maintained at this temperature for 15 hours. The aqueous phase was then extracted with Et2O (2×) and EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 1-(3-bromo-isoxazol-5-yl)-propan-1-one as an orange solid which was used without further purification.

Workup

  1. customwas transferred via a 16 gauge cannula to a 0° C.
  2. temperaturemaintained at this temperature for 15 hours
  3. extractionThe aqueous phase was then extracted with Et2O (2×) and EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20d02279aa0a447dbadca63c71e683a6
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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