N-bromobutanimide → HCID 69102910, compound

HRID 2250814Notes

Reaction equation

HRID 2250814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][Br:18])[C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69103145HCID 69103145, compound

Product 1

HCID 69102910HCID 69102910, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-4-methylbenzoxazole (P0001; 5.44 g), N-bromosuccinimide (4.77 g) and 2,2′-azobisisobutyronitrile (92 mg) in CCl4 (54 ml) was refluxed overnight. The insoluble was removed by filtration, and the filtrate was concentrated and cooled. The precipitates were collected and washed with CCl4 to give pale brown crystals of 2-(4-chlorophenyl)-4-(bromomethyl)benzoxazole (P0002; 6.31 g).

Workup

  1. temperaturewas refluxed overnight
  2. customThe insoluble was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. temperaturecooled
  5. customThe precipitates were collected
  6. washwashed with CCl4

Sources & evidence

ORD record
ord-c02d62cde47c43cd891b9feb5446e6cd
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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