Potassium Phosphate, Tribasic → 4-Ethoxy-2',3',4'-trifluoro-5-methyl-[1,1'-biphenyl]-2-carbaldehyde

HRID 402767ノート

反応式

HRID 402767 の反応式
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:51][C:52]1[C:57]([F:58])=[C:56]([F:59])[CH:55]=[CH:54][C:53]=1B(O)O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:12]([O:11][C:7]1[CH:6]=[C:3]([CH:4]=[O:5])[C:2]([C:55]2[CH:54]=[CH:53][C:52]([F:51])=[C:57]([F:58])[C:56]=2[F:59])=[CH:9][C:8]=1[CH3:10])[CH3:13]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 772308832-Bromo-5-ethoxy-4-methylbenzaldehyde

生成物 1

HCID 866768074-Ethoxy-2',3',4'-trifluoro-5-methyl-[1,1'-biphenyl]-2-carbaldehyde収率 66.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a degassed solution of 2-bromo-5-ethoxy-4-methylbenzaldehyde (300 mg, 1.31 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (53.8 mg, 0.131 mmol; S-Phos ligand) palladium (II) acetate (14.7 mg, 0.065 mmol) in THF (8 mL) were added K3PO4 (834 mg, 3.93 mmol) and (2,3,4-trifluorophenyl)boronic acid (276, 1.57 mmol). The reaction mixture was stirred at 70° C. under a N2 atmosphere for 16 hours, cooled to room temperature and filtered and the filtrate was concentrated by evaporation under reduced pressure. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to provide the title intermediate (255 mg) as white solid.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe residue was purified on a silica gel column
  5. washeluting with 5 to 10% EtOAc in hexanes

出典と根拠

ORDレコード
ord-103624b9257e4421b6ee88edb7a53404
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

反応ノート

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