Chlorobenzene → 1-(2-Bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 628498Notes

Reaction equation

HRID 628498 reaction equation
[CH3:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH3:15])[N:11]=[N:10]1.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.[Br:34]N1C(=O)CCC1=O.ClC1C=CC=CC=1>O>[Br:34][CH2:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH3:15])[N:11]=[N:10]1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 898758451-(2-Methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Product 1

HCID 898756621-(2-Bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-oneYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 10) 8.47 g, 1,1′-azobis(cyclohexane-1-carbonitrile) 1.54 g, N-bromosuccinimide 6.44 g and chlorobenzene 125 ml was stirred with heating under reflux for five hours. After cooling the mixture, to the reaction solutions was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one 7.52 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for five hours
  3. temperatureAfter cooling the mixture
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e460fcbef02470c831dfe27cca7debd
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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