Azobisisobutyronitrile → 3-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrile

HRID 1875067노트

반응식

HRID 1875067 반응식
[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH3:19])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.CCOC(C)=O>C(Cl)(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH2:19][Br:27])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6547AzobisisobutyronitrileHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 684846323-[(6-Bromo-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile

생성물 1

HCID 669997373-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrile수율 32.3%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8058Hexane용매

실험 절차

A mixture of 3-[(6-bromo-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile (3.39 g, 9.95 mmol), NBS (1.949 g, 10.95 mmol) and AIBN (0.082 g, 0.498 mmol) in carbon tetrachloride (45 ml) was heated at reflux overnight. The reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. Chromatography of the residue (EtOAc:hexane) gave 3-{[6-bromo-3-(bromomethyl)-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.35 g, 32.3% yield) as a colorless oil which crystallized to a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.44 (dd, 1H), 7.34 (s, 1H), 7.19-7.27 (m, 1H), 7.10-7.15 (m, 1H), 6.97 (s, 1H), 4.45 (s, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-0bd2f3a979ba46fd94d34f44de5f2a9a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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