N-Bromophthalimide → 1-[3-(bromomethyl)-4-fluorophenyl]-5-(trifluoromethyl)-1H-tetrazole

HRID 1006347Notes

Reaction equation

HRID 1006347 reaction equation
N(C(C)(CC(OC)(C)C)C#N)=NC(C)(CC(C)(OC)C)C#N.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]([C:35]([F:38])([F:37])[F:36])=[N:33][N:32]=[N:31]2)=[CH:26][C:25]=1[CH3:39].[Br:40]N1C(=O)C2=CC=CC=C2C1=O>ClCCl>[Br:40][CH2:39][C:25]1[CH:26]=[C:27]([N:30]2[C:34]([C:35]([F:38])([F:36])[F:37])=[N:33][N:32]=[N:31]2)[CH:28]=[CH:29][C:24]=1[F:23]

Participants

5

Reactant 3

HCID 75542N-BromophthalimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 226746621-(4-fluoro-3-methylphenyl)-5-(trifluoromethyl)-1H-tetrazole

Product 1

HCID 226746671-[3-(bromomethyl)-4-fluorophenyl]-5-(trifluoromethyl)-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2′-Azobis(4-methoxy-2,4-dimethylvaleronitrile) (50 mg) was added by three portions to the mixture of 1-(4-fluoro-3-methylphenyl)-5-(trifluoromethyl)-1H-tetrazole and N-bromophtalimide (1.44 g) in dichloromethane (16 ml) at 30° C. and the whole was stirred at reflux for 3 hours. After being cooled to room temperature, the mixture was washed with aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate successively. The organic layer was separated, dried over magnesium sulfate, and evaporated under reduced pressure to give a crude 1-[3-(bromomethyl)-4-fluorophenyl]-5-(trifluoromethyl)-1H-tetrazole (3:7).

Workup

  1. temperatureat reflux for 3 hours
  2. washthe mixture was washed with aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate successively
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a65cfe61ac354c4d84d5166498004d6e
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

Loading…