Benzoyl Peroxide → 2-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

HRID 7732

反応式

HRID 7732 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:37][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:4][C:3]=1[O:2][CH3:1]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 219909682-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

生成物 1

HCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole (1.0 g, 4.1 mmol), carbon tetrachloride (18 mL), benzoyl peroxide (66 mg, 0.3 mmol) and N-bromosuccinimide (970 mg, 5.4 mmol) was heated to reflux conditions under argon and placed under a UV light. After 1 h, no starting material was observed by TLC. After cooling mixture to rt, filtered, washing with dichoromethane. After concentrating filtrate in vacuo, the resulting colorless solid was purified by flash chromatography, using a gradient elution of 1:4 EtOAc:hexanes to EtOAc. This afforded the desired intermediate, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole, as a colorless solid.

後処理

  1. temperatureto reflux conditions under argon
  2. filtrationfiltered
  3. washwashing with dichoromethane
  4. concentrationAfter concentrating filtrate in vacuo
  5. customthe resulting colorless solid was purified by flash chromatography
  6. washa gradient elution of 1:4 EtOAc

出典と根拠

ORDレコード
ord-7b5dc4ac04c6402099cfcfbd4e02fa1a
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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