Azobisisobutyronitrile → 5-(Bromomethyl)benzo[d]oxazole

HRID 8957ノート

反応式

HRID 8957 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=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:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27249705-Methylbenzoxazole

生成物 1

HCID 219849815-(Bromomethyl)benzo[d]oxazole収率 39.6%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 5-methylbenzoxazole (200 mg, 1.50 mmol), N-bromosuccinimide (321 mg, 1.80 mmol), and 2,2′-azobisisobutyronitrile (37 mg, 0.23 mmol) in CCl4 (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 (5% EtOAc/hexanes) gave the title compound as a colourless crystals (126 mg, 39%). 1H NMR (CDCl3) δ 4.64 (s, 2H), 7.46 (dd, 1H, J=8.6, 1.7 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.83 (d, 1H, J=1.2 Hz), 8.12 (s, 1H).

後処理

  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 (5% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-5a8bb6473bd14813a5e1baaa37696a7d
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

反応ノート

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