Benzene, 1-bromo-4-(trifluoromethyl)- → 3,5-Difluoro-4-methyl-6-(4-trifluoromethylphenyl)-2-(3-trifluoromethylphenoxy)pyridine

HRID 382241Notes

Reaction equation

HRID 382241 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[CH3:17][C:18]1[C:23]([F:24])=[C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[N:21]=[C:20](F)[C:19]=1[F:37]>C(OCC)C>[F:24][C:23]1[C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)=[N:21][C:20]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[C:19]([F:37])[C:18]=1[CH3:17]

Participants

5

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 113012464-Methyl-2,3,5-trifluoro-6-(3-trifluoromethylphenoxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 187523663,5-Difluoro-4-methyl-6-(4-trifluoromethylphenyl)-2-(3-trifluoromethylphenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
10 °C

Procedure

Butyl lithium (2.6 ml, 6.6 mmol, 2.5 M solution in hexane) is added to a solution of 1-bromo-4-trifluoromethyl benzene (0.84 ml, 6 mmol) in anhydrous diethyl ether (5 ml) at −30° C. The mixture is stirred for 60 min at −20° C. and for 60 min at 10° C. The solution is allowed to warm to ambient temperature. This solution is then added to a mixture of 4-methyl-2,3,5-trifluoro-6-(3-trifluoromethylphenoxy)pyridine 2A (1.5 g, 5 mmol) in anhydrous diethyl ether (100 ml) at −50° C. during 2.5 hours. The mixture is further stirred for 7 hours at −50° C. and washed with saturated aqueous ammonium chloride and water. After drying and evaporation of the organic layer, the residue is purified by vacuum destillation. One obtains colorless crystals (0.37 g, 0.85 mmol, bp. 130° C. at 0.01-0.02 mbar) of mp. 87° C.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringThe mixture is further stirred for 7 hours at −50° C.
  3. washwashed with saturated aqueous ammonium chloride and water
  4. customAfter drying
  5. customevaporation of the organic layer
  6. customthe residue is purified by vacuum destillation
  7. customOne obtains colorless crystals (0.37 g, 0.85 mmol, bp. 130° C. at 0.01-0.02 mbar) of mp. 87° C.

Sources & evidence

ORD record
ord-aa58d48327024eb38f9dfaf2ba6ce417
Source dataset
uspto-grants-2001_10
Patent number
US06310006B1

Reaction notes

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