N-Bromosuccinamide → 5-(Bromomethyl)-2-(4-nitrophenyl)oxazole

HRID 880490Notes

Reaction equation

HRID 880490 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[N:4][CH:3]=1.[Br:16]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 9834204N-BromosuccinamideHCID 445506455-Methyl-2-(4-nitrophenyl)oxazole

Product 1

HCID 669147625-(Bromomethyl)-2-(4-nitrophenyl)oxazoleYield 65.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 5-methyl-2-(4-nitrophenyl)oxazole (3.2 g, 15.68 mmol) and benzoyl peroxide (10 mg, catalytic) in carbon tetrachloride (20 mL), was added N-bromo succinamide (2.77 g, 15.68 mmol). The mixture was heated to reflux for 9 h, filtered and the residue was washed with carbon tetrachloride. The combined filtrates were washed with water, sodium bicarbonate solution, brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified over silica gel (60-120 mesh) with 30% ethyl acetate/hexane as eluent to afford 5-(bromomethyl)-2-(4-nitro-phenyl)-oxazole (2.9 g, 65%) as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 9 h
  3. filtrationfiltered
  4. washthe residue was washed with carbon tetrachloride
  5. washThe combined filtrates were washed with water, sodium bicarbonate solution, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified over silica gel (60-120 mesh) with 30% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-7720dba8b4ab40339c6cc2f65ba8b55e
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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