5-Chloro-2-methoxyaniline → 5-Chloro-2-methoxy-beta-[3,5-bis(trifluoromethyl)phenyl]styrene

HRID 644458

반응식

HRID 644458 반응식
N([O-])=O.[Na+].N[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[O:13][CH3:14].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH:20]=[CH2:21]>O.[H+].[B-](F)(F)(F)F.CO.C(OCC)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([O:13][CH3:14])=[C:6]([CH:11]=1)[CH:21]=[CH:20][C:19]1[CH:22]=[C:23]([C:25]([F:26])([F:28])[F:27])[CH:24]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=1

참가 물질

8

반응물 3

HCID 667635-Chloro-2-methoxyanilineHCID 27732423,5-Bis(trifluoromethyl)styreneHCID 23668193Sodium Nitrite

생성물 1

HCID 765461385-Chloro-2-methoxy-beta-[3,5-bis(trifluoromethyl)phenyl]styrene수율 34.7%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 28118Tetrafluoroboric acid용매

반응 조건

온도
0 °C

실험 절차

A solution of sodium nitrite (57 mg, 0.8 mmol) in water (1 mL) was added to a solution of 2-amino-4-chloroanisole (131 mg, 0.8 mmol) in 48% hydrogen tetrafluoroborate (0.3 mL) under ice cooling and argon atmosphere. After the mixture was stirred at 0° C. for 1 hour, a solution of 3,5-bis(trifluoromethyl)styrene (100 mg, 0.4 mmol) in methanol (3 mL) was added and the mixture was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, the residue obtained by evaporation of the solvent under reduced pressure was diluted with ethyl acetate. After the solution was washed successively with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (52.8 mg, 33.3%) as a white powder.

후처리

  1. stirringthe mixture was stirred at 50° C. for 1 hour
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe residue obtained by evaporation of the solvent under reduced pressure
  4. washAfter the solution was washed successively with 2N hydrochloric acid, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-84c38d26b4db498692231614c5f962f7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700655B2

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