Toluene → 2-Amino-6-methyl-5-(3-fluoro-5-trifluoromethylphenyl)benzonitrile

HRID 363779ノート

反応式

HRID 363779 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:28]2[CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=[C:26]([F:25])[CH:27]=2)=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5]

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27831923-Fluoro-5-(trifluoromethyl)benzeneboronic acidHCID 224657376-Amino-3-bromo-2-methylbenzonitrile

生成物 1

HCID 545688402-Amino-6-methyl-5-(3-fluoro-5-trifluoromethylphenyl)benzonitrile収率 103%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

Under a dry nitrogen atmosphere, 0.5 gram (0.0004 mole) of tetrakis(triphenylphosphine)palladium(0) was added to a stirred mixture of 2.8 grams (0.0132 mole) of 2-amino-5-bromo-6-methylbenzonitrile (prepared as in Step C of Example 1), 35 mL of aqueous 2M sodium carbonate and 50 mL of toluene. To this was then added dropwise a solution of 3.3 grams (0.0159 mole) of 3-fluoro-5-trifluoromethylphenylboronic acid in 10 mL of ethanol. Upon completion of addition, the reaction mixture was warmed to about 80° C., where it was stirred for seven hours. After this time the reaction mixture was poured into 200 mL of water. The mixture was then extracted with four 100 mL portions of ethyl acetate. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.0 grams of 2-amino-6-methyl-5-(3-fluoro-5-trifluoromethylphenyl)benzonitrile, mp 96°-97° C. The NMR spectrum was consistent with the proposed structure.

後処理

  1. additionUpon completion of addition
  2. extractionThe mixture was then extracted with four 100 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue
  6. washElution
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b583c4ae6dcd478b86aafb825d72723d
出典データセット
uspto-grants-1999_02
特許番号
US05874579

反応ノート

読み込み中…