Triethylamine → 2-Bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone

HRID 910221Notes

Reaction equation

HRID 910221 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[Br:22][Si](C)(C)C>ClCCl>[Br:22][CH2:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]([C:5]2[O:1][CH:2]=[N:3][CH:4]=2)=[CH:11][CH:10]=1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76113BromotrimethylsilaneHCID 223169301-[4-(1,3-Oxazol-5-yl)phenyl]ethan-1-one

Product 1

HCID 866318862-Bromo-1-[4-(1,3-oxazol-5-yl)phenyl]-1-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-(1,3-Oxazol-5-yl)phenyl]-1-ethanone (2.81 g) and triethylamine (6.27 mL) were dissolved in dichloromethane mL), and bromotrimethylsilane (3.96 mL) was added dropwise to the solution under ice cooling. The mixture was stirred at room temperature overnight under argon. The reaction mixture was washed sequentially with water and saturated saline, followed by drying over magnesium sulfate. The solvent was evaporated under reduced pressure, and the formed brown oily matter was dissolved in tetrahydrofuran mL). Subsequently, N-bromosuccinimide (2.67 g) was added to the solution, followed by stirring at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and the residue was purified through flash column chromatography (dichloromethane), followed by concentration under reduced pressure. The obtained solid was recovered through filtration by use of n-hexane, to thereby yield the title compound (3.35 g).

Workup

  1. additionwas added dropwise to the solution under ice cooling
  2. washThe reaction mixture was washed sequentially with water and saturated saline
  3. dry with materialby drying over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe formed brown oily matter was dissolved in tetrahydrofuran mL)
  6. additionSubsequently, N-bromosuccinimide (2.67 g) was added to the solution
  7. stirringby stirring at room temperature for 30 minutes
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with ethyl acetate
  10. customThe solvent was evaporated
  11. customthe residue was purified through flash column chromatography (dichloromethane)
  12. concentrationfollowed by concentration under reduced pressure
  13. filtrationThe obtained solid was recovered through filtration by use of n-hexane

Sources & evidence

ORD record
ord-9c793b7f31884a02a6c96be51f38a382
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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