Reaction #1833284

Reaction equation

2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene

4-nitropyrazole

potassium carbonate

2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene

→

title compound

Yield 86.2%

1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-4-nitro-1H-pyrazole

Yield 86.2%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction was stirred at ambient temperature for a further 30 min
2. 2
   ConcentrationThe reaction mixture was concentrated in vacuo
3. 3
   workup.ADDITIONtreated with water (60 ml)
4. 4
   ExtractionThe aqueous solution was extracted with ethyl acetate (3×60 ml)
5. 5
   DryingThe combined organic layers were dried (MgSO4)
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherpurified on silica (50 g)
8. 8
   Otherevaporated in vacuo

Procedure

To a solution of 4-nitropyrazole (Manchester organics; 0.503 g, 4.45 mmol) in DMF (10 ml) was added potassium carbonate (1.24 g, 9.0 mmol), sodium iodide (24 mg, 0.160 mmol) and then 2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (synthesised according to WO2006066968; 1.23 g, 3.95 mmol). The reaction was stirred at ambient temperature overnight. A further amount of 2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (156 mg) was added and the reaction was stirred at ambient temperature for a further 30 min. The reaction mixture was concentrated in vacuo and treated with water (60 ml). The aqueous solution was extracted with ethyl acetate (3×60 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica (50 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.17 g) as a white solid; LCMS (System 1): MH+=344, tRET=3.58 min.

Source