Toluene → 4'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile

HRID 519498ノート

反応式

HRID 519498 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1OB(O)O)#[N:15].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:17]2[C:16]([C:14]#[N:15])=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:3][C:4]=1[C:10]([F:13])([F:12])[F:11])=[O:7]

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 121872184-Bromo-2-(trifluoromethyl)benzaldehydeHCID 217080892-Cyano-phenylboric acid

生成物 1

HCID 866440264'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile収率 32.7%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-2-(trifluoromethyl)benzaldehyde (9 g), 2-cyano-phenylboric acid (9.5 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (2.9 g), tetrabutylammonium bromide (1.15 g), 2M aqueous sodium carbonate solution (30 mL) and toluene (100 mL) was stirred at 100° C. overnight under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 32%).

後処理

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c9feda5c388842dfb335337ba5cd470b
出典データセット
uspto-grants-2015_08
特許番号
US09115136B2

反応ノート

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