Benzoyl Peroxide → 5-(4-Bromomethylphenyl)-2-methyl-2H-tetrazole

HRID 1642020Notes

Reaction equation

HRID 1642020 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:3]1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[N:5]=[N:6][N:2]([CH3:1])[N:3]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5896862-Methyl-5-(4-methylphenyl)tetrazole

Product 1

HCID 5893295-(4-Bromomethylphenyl)-2-methyl-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 45 grams (0.258 mole) of 2-methyl-5-(4-methylphenyl)-1,2,3,4-tetrazole (known compound), 46 grams (1 equivalent) of N-bromosuccinimide, and a catalytic amount of benzoyl peroxide in 200 mL of carbon tetrachloride was irradiated with light during a 3.5 hour period. The mixture was then cooled in an ice bath and filtered to collect 35.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. filtrationfiltered
  3. customto collect 35.1 grams of the subject compound

Sources & evidence

ORD record
ord-d413d45402404e7bb5cfeed142e815f3
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

Loading…