N-bromobutanimide → 6'-Methyl-2'-bromomethyl-2-(4-methoxybenzoyl)-biphenyl-4-carbonitrile

HRID 1359151

반응식

HRID 1359151 반응식
CO[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=2[C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[C:5]([CH3:28])[CH:4]=1.C1C(=O)N([Br:36])C(=O)C1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:28][C:5]1[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=2[C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[C:7]([CH2:9][Br:36])[CH:8]=[CH:3][CH:4]=1

참가 물질

6

반응물 3

HCID 67184N-bromobutanimideHCID 108940114'-Methoxy-2',6'-dimethyl-2-(4-methoxybenzoyl)-biphenyl-4-carbonitrileHCID 86630000Nbs aibn

생성물 1

HCID 181827486'-Methyl-2'-bromomethyl-2-(4-methoxybenzoyl)-biphenyl-4-carbonitrile수율 93.6%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매2회HCID 5943Carbon Tetrachloride용매

실험 절차

To a refluxing solution of the compound from Step D (45.5 g, 122 mmol) and AIBN (1.0 g) in CCl4 (2.5 L) was added a mixture of NBS (23.0 g, 129 mmol) and AIBN (1.0 g) in ten equal portions. The reaction mixture was refluxed for 2 h after the addition of the last portion of NBS/AIBN. The reaction mixture was concentrated to approximately 1 L and washed 3 times with water (1 L). The organic layer was dried with anhydrous Na2SO4, filtered and the solvent removed. Toluene (200 ml) was added to the residue and then evaporated. Repeating this procedure gave 48 g of the title compound that was used without further purification.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. concentrationThe reaction mixture was concentrated to approximately 1 L
  3. washwashed 3 times with water (1 L)
  4. dry with materialThe organic layer was dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. additionToluene (200 ml) was added to the residue
  8. customevaporated

출처 및 근거

ORD 기록
ord-3ec49c2663994f3995567c06e06a9d32
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599921B2

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