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

HRID 251307노트

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HRID 251307 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b46b7aad42a419ab7bb1e1121eb0808
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863329B2

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