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

HRID 855921노트

반응식

HRID 855921 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da08ae807ecd4cb68994eda87ea96232
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262301B1

반응 노트

불러오는 중…