Boron tribromide → 2-(3-hydroxyphenyl)quinazolin-4(3H)-one

HRID 1406879ノート

反応式

HRID 1406879 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:18][C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:18][C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 1354863992-(3-methoxyphenyl)quinazolin-4(3H)-one

生成物 1

HCID 1355672462-(3-hydroxyphenyl)quinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To 2-(3-methoxyphenyl)quinazolin-4(3H)-one (11.6 g, 45.98 mmole) was added of CH2Cl2 (120 mL) and the mixture was cooled to −78° C. Then, a 1 M solution of BBr3 in CH2Cl2 (60 mL, 60.0 mmol) was added drop wise and the reaction was stirred at −78° C. for 1 h and then ambient temperature for 3 h. The reaction was re-cooled to −78° C. and cautiously quenched with MeOH (20 mL). The ice bath was removed and the system allowed to stir at ambient temperature for 0.5 h. The pH was adjusted to 7 with 10% w/w NaHCO3 solution. The solid was filtered, washed with ether, dried and then azeotroped from toluene (3×) and dried under high vacuum overnight to give 2-(3-hydroxyphenyl)quinazolin-4(3H)-one. (11.0 g, mmol, 100%).

後処理

  1. waitambient temperature for 3 h
  2. temperatureThe reaction was re-cooled to −78° C.
  3. customcautiously quenched with MeOH (20 mL)
  4. customThe ice bath was removed
  5. stirringto stir at ambient temperature for 0.5 h
  6. filtrationThe solid was filtered
  7. washwashed with ether
  8. customdried
  9. customazeotroped from toluene (3×)
  10. customdried under high vacuum overnight

出典と根拠

ORDレコード
ord-d6abae01e8684fa7b87fe1d9883e107f
出典データセット
uspto-grants-2014_12
特許番号
US08916576B2

反応ノート

読み込み中…