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

HRID 628489Notes

Reaction equation

HRID 628489 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]1.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.[Br:37]N1C(=O)CCC1=O.ClC1C=CC=CC=1>O>[Br:37][CH2:1][C:2]1[C:7]([O:8][CH:9]([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 898759001-(2-Methyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Product 1

HCID 898812151-(2-Bromomethyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-oneYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(2-methyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 2) 1.0 g, 1,1′-azobis(cyclohexane-1-carbonitrile) 0.19 g, N-bromosuccinimide 0.80 g and chlorobenzene 50 ml was stirred with heating under reflux for eight 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-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 1.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for eight 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-26a0a192357e4705a25d68bf9d82fca8
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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