Azobisisobutyronitrile → 4-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole

HRID 855921ノート

反応式

HRID 855921 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][O:21][CH3:22])=[C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=3[N:13]=2)[CH:8]=1.[Br:23]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:18][C:14]1[C:12]2[N:13]=[C:9]([C:7]3[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[O:19][CH2:20][O:21][CH3:22])[O:10][C:11]=2[CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 219593252-(5-Methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole

生成物 1

HCID 219593264-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole収率 76.4%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) (1.78 g, 5.95 mmol), N-bromosuccinimide (1.01 g, 5.95 mmol), and AIBN (82 mg, 0.5 mmol) in CCl4 (100 mL) was refluxed for 15 h under dry N2 gas flowing. The reaction mixture was cooled to 0° C., the precipitation was removed by filtration maintaining the temperature. After the solvent was evaporated, the residue was washed with small amount of ethanol several times to afford a pinkish solid (1.72 g, 76%). 1H-NMR (500 MHz, CDCl3) δ3.57 (s, 3H), 3.88 (s, 3H), 4.96 (s, 2H), 5.27 (s, 2H), 7.05 (dd, 1H, J=8.5, 3.0 Hz), 7.22 (d, 1H, J=8.5 Hz), 7.34 (t, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.54 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=3.0 Hz).

後処理

  1. temperaturewas refluxed for 15 h under dry N2 gas
  2. customthe precipitation
  3. customwas removed by filtration
  4. temperaturemaintaining the temperature
  5. customAfter the solvent was evaporated
  6. washthe residue was washed with small amount of ethanol several times

出典と根拠

ORDレコード
ord-da08ae807ecd4cb68994eda87ea96232
出典データセット
uspto-grants-2007_08
特許番号
US07262301B1

反応ノート

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