Hydrochloric Acid → 3-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

HRID 1957235Notes

Reaction equation

HRID 1957235 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][C:15]=1[O:23][CH3:24].C(=O)(O)[O-].[Na+].Cl>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:8][C:7]1[C:2]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[C:15]([O:23][CH3:24])[CH:16]=2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 516892Sodium BicarbonateHCID 23005377(4-Chloro-3-methoxyphenyl)boronic acid

Product 1

HCID 157668763-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

38.8 g (0.180 mol) of 2,3-dichloro-5-trifluoromethylpyridine, 33.5 g (0.180 mol) of 4-chloro-3-methoxybenzeneboronic acid, 0.7 g (0.61 mmol) of tetrakis(triphenylphosphine)palladium(O) and 45.3 g (0.539 mol) of sodium bicarbonate in a mixture of 550 ml of dimethoxyethane and 550 ml of water were refluxed for four hours. The mixture was then acidified to pH 4-5 with dilute hydrochloric acid, the dimethoxyethane was removed by distillation, and the remaining aqueous phase was extracted with methylene chloride. The combined methylene chloride phases were washed with water, dried over sodium sulfate and evaporated. The residue was stirred with a little cold n-hexane, filtered off with suction and dried. Yield: 44.2 g (76%) of colorless crystals of melting point 72° C.

Workup

  1. temperaturewere refluxed for four hours
  2. customthe dimethoxyethane was removed by distillation
  3. extractionthe remaining aqueous phase was extracted with methylene chloride
  4. washThe combined methylene chloride phases were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-8b8f5deeef36419ba21a77359e60fb53
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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