Potassium Phosphate, Tribasic → HCID 87088131、化合物

HRID 402763ノート

反応式

HRID 402763 の反応式
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[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:50][C:51]1[C:56]([F:57])=[C:55]([F:58])[CH:54]=[CH:53][C:52]=1B(O)O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:7]1[CH:6]=[C:3]([CH:4]=[O:5])[C:2]([C:54]2[CH:53]=[CH:52][C:51]([F:50])=[C:56]([F:57])[C:55]=2[F:58])=[CH:9][CH:8]=1)[CH3:12]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 30164192-Bromo-5-ethoxybenzaldehydeHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

生成物 1

HCID 87088131HCID 87088131、化合物収率 69.5%

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-ethoxybenzaldehye (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). Reaction mixture was stirred at 70° C. under a N2 atmosphere for 16 hours, cooled to room temperature and then filtered. 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. customReaction mixture
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. customThe residue was purified on a silica gel column
  6. washeluting with 5 to 10% EtOAc in hexanes

出典と根拠

ORDレコード
ord-b6fd571bca3d487695db922439a541ef
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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