Benzene, 1-bromo-4-(trifluoromethyl)- → 4-Methyl-2,3,5-trifluoro-6-(4-trifluoromethylphenyl)pyridine

HRID 382239노트

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HRID 382239 반응식
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](F)[N:21]=[C:20]([F:26])[C:19]=1[F:27]>C(OCC)C>[CH3:17][C:18]1[C:23]([F:24])=[C:22]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[N:21]=[C:20]([F:26])[C:19]=1[F:27]

참가 물질

5

반응물 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 46613162,3,5,6-Tetrafluoro-4-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 114377574-Methyl-2,3,5-trifluoro-6-(4-trifluoromethylphenyl)pyridine수율 25.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
10 °C

실험 절차

Butyl lithium (2.7 ml, 6.7 mmol, 2.5 M solution in hexane) is added to a solution of 1-bromo-4-trifluoromethyl benzene (1.0 ml, 7.3 mmol) in anhydrous diethyl ether (10 ml) at −20° C. The mixture is stirred for 60 min at −20° C. and for 60 min at 10° C. After cooling to −40° C. 4-methyl-2,3,5,6-tetrafluoropyridine (1.1 g, 6.6 mmol) is added. The resulting mixture is stirred for 120 min at −30° C. and then is allowed to warm to ambient temperature. After 2 days at ambient temperature the mixture is washed twice with saturated aqueous ammonium chloride. The layers are separated and the organic layer is dried with anhydrous magnesium sulfate and filtered. After removal of the solvents in vacuo, the crude product is purified by flash column chromatography (silica gel, pentane/ethyl acetate=9/1 by volume) yielding colorless crystals of 4-methyl-2,3,5-trifluoro-6-(4-trifluoromethylphenyl)pyridine (0.5 g, 1.7 mmol) of mp. 52° C.

후처리

  1. temperatureAfter cooling to −40° C
  2. stirringThe resulting mixture is stirred for 120 min at −30° C.
  3. temperatureto warm to ambient temperature
  4. washAfter 2 days at ambient temperature the mixture is washed twice with saturated aqueous ammonium chloride
  5. customThe layers are separated
  6. dry with materialthe organic layer is dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customAfter removal of the solvents in vacuo
  9. customthe crude product is purified by flash column chromatography (silica gel, pentane/ethyl acetate=9/1 by volume)

출처 및 근거

ORD 기록
ord-ee171283d4294b6ba526a0a7e0010c8b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310006B1

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