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

HRID 382241
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HRID 382241 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]([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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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온도
10 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-aa58d48327024eb38f9dfaf2ba6ce417
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06310006B1

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