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

HRID 644458

反応式

HRID 644458 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 28118Tetrafluoroboric acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-84c38d26b4db498692231614c5f962f7
出典データセット
uspto-grants-2010_04
特許番号
US07700655B2

関連ノート

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