Potassium Carbonate → 3',4',5'-Trifluoro-[1,1'-biphenyl]-4-carbaldehyde

HRID 1406828

反応式

HRID 1406828 の反応式
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22](OB(O)O)=[CH:21][CH:20]=1)=[O:18]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 21940015p-Formylphenylboric acid

生成物 1

HCID 612398773',4',5'-Trifluoro-[1,1'-biphenyl]-4-carbaldehyde収率 96.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

In a nitrogen atmosphere, a solution prepared by mixing 15.00 g of 3,4,5-trifluorobromobenzene, 0.25 g of tetrakis-triphenylphosphine palladium, 30 mL of an aqueous potassium carbonate solution (2 mol/L), and 75 mL of THF was heated to 60° C., and 10.71 g of 4-formylphenylboric acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 14.77 g of 4-(3,4,5-trifluorophenyl)benzaldehyde was yielded.

後処理

  1. customIn a nitrogen atmosphere, a solution prepared
  2. temperatureto cool
  3. customan organic layer was separated
  4. additionby adding hexane
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. additionby adding sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customAs a result of purification by silica gel column chromatography

出典と根拠

ORDレコード
ord-1f4bff464cbe48f4820367ccdde28900
出典データセット
uspto-grants-2014_12
特許番号
US08916718B2

関連ノート

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