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

HRID 1359151
Notes
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Reaction equation

HRID 1359151 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6547
Azobisisobutyronitrile
Catalyst
2×
HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ec49c2663994f3995567c06e06a9d32
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06599921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes