Sodium Hydroxide → 1-(3-trifluoromethylbenzyl)-1H-benzotriazole

HRID 1019168Notes

Reaction equation

HRID 1019168 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[OH-].[Na+].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br>CN(C=O)C.O>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 178418385HCID 178418385, compound

Product 1

HCID 46521561-(3-trifluoromethylbenzyl)-1H-benzotriazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzotriazole (3 g) in DMF (38 mL) at r.t. was added a solution of 10N NaOH (2.75 mL). After stirring for 25 min., 3-trifluoromethylbenzyl bromide (4.39 mL) was added. The mixture was further stirred for 30 min., diluted with H2O, and extracted with EtOAc. The EtOAc extract was washed brine (2×), water, brine, dried (MgSO4) and concentrated. The residue was stirred in diethyl ether/hexane to afford 3.96 g of the title compound as a white solid.

Workup

  1. stirringThe mixture was further stirred for 30 min.
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed brine (2×), water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. stirringThe residue was stirred in diethyl ether/hexane

Sources & evidence

ORD record
ord-18412748e0d54ac2b3467132de7dac4d
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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