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3-(Trifluoromethyl)phenol → 2-(Methylsulfanyl)-4-(trifluoromethyl)-6-[3-(trifluoromethyl)phenoxy]pyrimidine

HRID 802
Notes
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Reaction equation

HRID 802 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:18]=[C:17]([S:25][CH3:26])[N:16]=1>C1COCC1>[CH3:26][S:25][C:17]1[N:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 2480634-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 14750002-(Methylsulfanyl)-4-(trifluoromethyl)-6-[3-(trifluoromethyl)phenoxy]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. additionVII-17) (1.0 g, 0.0044 mol) was added
  2. temperatureThe resulting solution was refluxed for about 7 hours
  3. customThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  4. customto separate an organic phase
  5. washThe organic phase was washed with aqueous saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. distillationwere distilled off in a tubular oven (under water flow, 150° C.)
  9. customto obtain the intermediate compound

Sources & evidence

ORD record
ord-779700042b074f55b42f3a2202e7c555
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723412

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes