Potassium Carbonate → 2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-carbaldehyde

HRID 251307ノート

反応式

HRID 251307 の反応式
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:18])[CH:4]=1)=[O:2].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[Li+].[Cl-].C([O-])([O-])=O.[K+].[K+]>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>[CH3:18][C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[CH:8]=[C:7]([CH3:9])[C:6]=1[C:24]1[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 544771104-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

生成物 1

HCID 860853062,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-carbaldehyde収率 96.2%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

Trifluoro-methanesulfonic acid 4-formyl-2,6-dimethyl-phenyl ester (4 g, 14.2 mmol), 4-trifluoromethyl-phenylboronic acid (5.4 g, 28.4 mmol), tetrakis(triphenylphosphine)palladium (1.64 g, 1.42 mmol), LiCl (1.8 g, 42.6 mmol), and K2CO3 (5.9 g, 42.6 mmol) are placed in a flask. The system is purged with nitrogen, followed by the addition of toluene (20 ml) and water (5 ml). The resulting mixture is refluxed overnight, loaded on silica gel directly, and purified by silica gel column chromatography, eluting with EtOAc/hexanes to afford 3.8 g (96%) of the titled compound as a white solid. 1H-NMR.

後処理

  1. customThe system is purged with nitrogen
  2. additionfollowed by the addition of toluene (20 ml) and water (5 ml)
  3. temperatureThe resulting mixture is refluxed overnight
  4. custompurified by silica gel column chromatography
  5. washeluting with EtOAc/hexanes

出典と根拠

ORDレコード
ord-3b46b7aad42a419ab7bb1e1121eb0808
出典データセット
uspto-grants-2011_01
特許番号
US07863329B2

反応ノート

読み込み中…