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

HRID 1656402Notes

Reaction equation

HRID 1656402 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:18]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]=[N:16][N:15]=2)=[CH:4][CH:3]=1.[Br:38]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:38][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:18]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]=[N:16][N:15]=2)=[CH:6][CH:7]=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

4-Methyl-2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl (52.07 g, 109 mmol, 1 eq; for preparation, see Example 95, Part B), N-bromosuccinimide (19.4 g, 109 mmol, 1 eq), benzoyl peroxide (1.0 g) and carbon tetrachloride (300 mL) were mixed and refluxed for 2.5 h. The reaction was cooled to room temperature and the succinimide filtered. The filtrate was concentrated and the residue triturated with ether to yield a first crop of 36.0 g:mp 129.5°-133.0° C. (dec.). NMR (CDCl3) δ 4.37 (CH2Br). This material was suitable for further transformation. ##STR77##

Workup

  1. temperaturerefluxed for 2.5 h
  2. filtrationthe succinimide filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue triturated with ether
  5. customto yield a first crop of 36.0 g

Sources & evidence

ORD record
ord-c44cd93853f94675a681cbadd5547bec
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

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