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

HRID 7732

반응식

HRID 7732 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b5dc4ac04c6402099cfcfbd4e02fa1a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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