Azobisisobutyronitrile → 6-(Bromomethyl)benzo[d]oxazole

HRID 8958Notes

Reaction equation

HRID 8958 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27249696-Methylbenzoxazole

Product 1

HCID 219850576-(Bromomethyl)benzo[d]oxazoleYield 38.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-methylbenzoxazole (422 mg, 3.17 mmol), N-bromosuccinimide (677 mg, 3.80 mmol), and 2,2′-azobisisobutyronitrile (78 mg, 0.48 mmol) in CCl4 (6.3 mL) was heated at reflux for 22 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the crude material on silica gel (4% EtOAc/hexanes) gave the title compound as colourless crystals (257 mg, 38%). 1H NMR (CDCl3) δ 4.64 (s, 2H), 7.42 (dd, 1H, J=8.1, 1.5 Hz), 7.64 (d, 1H, J=1.2 Hz), 7.76 (d, 1H, J=8.4 Hz), 8.12 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification of the crude material on silica gel (4% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e3cc0077e4c14e81be0b4dc412ae5316
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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