Sodium Hydroxide → 1-[(4-fluorophenyl)methyl]benzotriazole

HRID 1019166Notes

Reaction equation

HRID 1019166 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]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CN(C=O)C.O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[N:2]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 178418385HCID 178418385, compound

Product 1

HCID 7336221-[(4-fluorophenyl)methyl]benzotriazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzotriazole (12 g) in DMF (150 mL) at r.t. was added a solution of 10N NaOH (11 mL). After stirring for 30 min., 4-fluorobenzyl bromide (3.9 mL) was added. The mixture was further stirred for 3 hrs, diluted with H2O, and extracted with EtOAc. The EtOAc extract was washed water (2×), dried (MgSO4) and concentrated. The residue was stirred in diethyl ether/hexane to afford the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-429abae52906427e93f940c7c0edc4f4
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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