1-[(4-fluorophenyl)methyl]benzotriazole → 1-fluoro-4-[2-(4-fluorophenyl)ethynyl]benzene

HRID 1492662Notes

Reaction equation

HRID 1492662 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]N2C3C=CC=CC=3N=N2)=[CH:10][CH:9]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]=NC2C=CC=CC=2)=[CH:27][CH:26]=1>CN(C=O)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7336221-[(4-fluorophenyl)methyl]benzotriazoleHCID 918392N-(4-Fluorobenzylidene)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 52405331-fluoro-4-[2-(4-fluorophenyl)ethynyl]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To potassium t-butoxide (1.5 g, 13.4 mmol) in DMF (15 mL) at 75° C. was added as quickly as possible and all at once [(4-fluorophenyl)methyl]-1H-benzotriazole (1.14 g, 5 mmol) and (4-fluorophenyl)methylenebenzenamine (1.00 g, 5 mmol) dissolved in DMF (10 mL). Within a minute the solution is poured into ice-cold water (75 mL) crystallizing the title compound which was filtered and then chromatographed (PE). The acetylene 0.54 g (50%) recrystallizes as needles: mp 95°-96° C. (MeOH); (lit.1 94°-95° C.).

Workup

  1. customcrystallizing the title compound which
  2. filtrationwas filtered
  3. customchromatographed (PE)
  4. customThe acetylene 0.54 g (50%) recrystallizes as needles
  5. custom(lit.1 94°-95° C.)

Sources & evidence

ORD record
ord-5e7bef54be0848aa927106a72e80686c
Source dataset
uspto-grants-1994_12
Patent number
US05374701

Reaction notes

Loading…