4-Fluoro-3-(trifluoromethyl)phenol → HCID 15477722, compound

HRID 2305395Notes

Reaction equation

HRID 2305395 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C:5]([Cl:16])=[CH:4][N:3]=1.CN(C)C.C1(C)C=CC=CC=1.[F:28][C:29]([F:39])([F:38])[C:30]1[CH:31]=[C:32]([OH:37])[CH:33]=[CH:34][C:35]=1[F:36]>C1(C)C=CC=CC=1.O>[F:39][C:29]([F:28])([F:38])[C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][C:35]=1[F:36])[O:37][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C:5]([Cl:16])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6018544-Fluoro-3-(trifluoromethyl)phenolHCID 15477739HCID 15477739, compoundHCID 19884236HCID 19884236, compound

Product 1

HCID 15477722HCID 15477722, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 0.5 g (1.7 mmol) of 3B in 10 mL of toluene was added 4.0 mL of 10% trimethylamine/toluene solution and the mixture stirred at room temperature for 20 min. To the resulting mixture was added 0.36 g (20 mmol) of 3-trifluoromethyl-4-fluorophenol and the mixture stirred overnight. The reaction mixture was diluted with H2O and transferred to a separatory funnel and extracted with 40 mL of methylene chloride. The organic layer was washed sequentially with 5% NaHCO3 solution and water, dried and evaporated to yield 0.52 g (70.3%) of 2-(3-trifluoromethyl-4-fluorophenoxy)-4-(3,4-dichlorophenyl)-5-chloropyrimidine (m.p. 90-92)

Workup

  1. stirringthe mixture stirred overnight
  2. customtransferred to a separatory funnel
  3. extractionextracted with 40 mL of methylene chloride
  4. washThe organic layer was washed sequentially with 5% NaHCO3 solution and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-eb37de5e5dc44753aa1b2d8a5b0d8300
Source dataset
uspto-grants-2002_08
Patent number
US06440984B1

Reaction notes

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