Hydrogen Bromide → HCID 86652406, compound

HRID 1529050Notes

Reaction equation

HRID 1529050 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[C:14](Cl)=[O:15])=[CH:4][CH:3]=1.[CH3:17][Si](C=[N+]=[N-])(C)C.[BrH:24]>C(#N)C>[Br:24][CH2:17][C:14]([C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 866524055-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbonyl chloride

Product 1

HCID 86652406HCID 86652406, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbonyl chloride (from the previous step) was dissolved in ACN (30 mL) then trimethylsilyl-diazomethane (2M in Et2O, 16.38 mL, 32.76 mmol) was slowly added and the reaction stirred at room temperature for 2 hours. Hydrobromic acid (30% aq., 7 mL) was carefully added and the reaction stirred for an additional 1 hour. The mixture was submitted to standard aqueous workup then purified on silica gel (0-20% EtOAc in hexanes) to afford the title compound.

Workup

  1. stirringthe reaction stirred for an additional 1 hour
  2. customthen purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-29d3180ebfaf450cbf9ce2905b369e34
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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