Benzoyl Peroxide → 5-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

HRID 1197582Notes

Reaction equation

HRID 1197582 reaction equation
[C:1]1([C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:38]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:32]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][Br:38])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 101520195-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazole

Product 1

HCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-triphenylmethyl-5 (4'-methylbiphenyl-2-yl)tetrazole (Example 11, 12.7 g), N-bromosuccinimide (4.6 g), carbon tetrachloride (300 mL), and benzoyl peroxide (75 mg) was heated at reflux for 2.5 hours. The cooled suspension was filtered and the filtrate was evaporated to give the title compound as a crystalline solid. 1H-NMR (CDCl3) δ8.2-6.7 (complex, 23H), 4.3 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationThe cooled suspension was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-727829b2058b476d9d67db81590c3209
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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