Benzoyl Peroxide → 6-Acetyl-3-(bromomethyl)-4-chloro-3'-fluorobiphenyl-2-carbonitrile

HRID 1192589노트

반응식

HRID 1192589 반응식
[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH2:19][Br:21])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

생성물 1

HCID 583686246-Acetyl-3-(bromomethyl)-4-chloro-3'-fluorobiphenyl-2-carbonitrile수율 45%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carbonitrile (1.00 g, 3.48 mmol), N-bromosuccinimide (0.650 g, 3.65 mmol), and benzoyl peroxide (0.0421 g, 0.174 mmol) in carbon tetrachloride (10 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was diluted with dichloromethane and washed with water. The organic layers were dried over magnesium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to give the desired product (0.57 g, 45%). LCMS calculated for C16H11BrClFNO (M+H)+: m/z=366.0; Found: 366.0.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with water
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-41a08f3671cd43adab0aa1e4eb33e566
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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