Reaction #898

Reaction equation

m-(Trifluoromethyl)phenol

NaH

4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine

→

2-methylthio-4-trifluoromethyl-6-[3-(trifluoromethyl)phenoxy]pyrimidine

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONVII-17) (1.0 g, 0.0044 mol) was added
2. 2
   TemperatureThe resulting solution was refluxed for about 7 hours
3. 3
   OtherThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
4. 4
   Otherto separate an organic phase
5. 5
   WashThe organic phase was washed with aqueous saturated sodium chloride
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   workup.DISTILLATIONwere distilled off in a tubular oven (under water flow, 150° C.)
9. 9
   Otherto obtain the intermediate compound

Procedure

m-(Trifluoromethyl)phenol (1.06 g, 0.0044×1.5 mol) and NaH (0.26 g (ca.60% in mineral oil), 0.0044×1.5 mol) were dissolved in THF, and then 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (Compound No. VII-17) (1.0 g, 0.0044 mol) was added thereto. The resulting solution was refluxed for about 7 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated. Thereafter, remaining phenol and others were distilled off in a tubular oven (under water flow, 150° C.) to obtain the intermediate compound.

Source