Ethanone, 1-(2-chlorophenyl)- → 2-[4-Chloro-3-(methyloxy)phenyl]-1-(2-chlorophenyl)-ethanone

HRID 1673253

反応式

HRID 1673253 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Br[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[O:10])=[CH:13][C:14]=1[O:19][CH3:20]

参加物

7

反応物 4

HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 27695675-Bromo-2-chloroanisoleHCID 23676156Sodium t-butoxide

生成物 1

HCID 673304672-[4-Chloro-3-(methyloxy)phenyl]-1-(2-chlorophenyl)-ethanone

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(2-chlorophenyl)ethanone (1.4 mL, 10.8 mmol), 4-bromo-1-chloro-2-(methyloxy)benzene (2.0 g, 9.0 mmol), sodium tert-butoxide (2.2 g, 22.6 mmol), palladium(II) acetate (20.3 mg, 0.1 mmol), and 2-(dicyclohexylphosphino)-2′-methylbiphenyl (65.8 mg, 0.2 mmol) in 30 mL of toluene was degassed and stirred at 80° C. for 16 h. The reaction mixture was cooled and a mixture of Et2O (100 mL) and H2O (100 mL) was added. The aq layer was separated and extracted with Et2O (3×50 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 3.87 (s, 3H), 4.22 (s, 2H), 6.75 (dd, J=1.7, 8.2, 1H), 6.81 (d, J=1.6, 1H), 7.26-7.31 (m, 2H), 7.37-7.43 (m, 3H).

後処理

  1. customwas degassed
  2. temperatureThe reaction mixture was cooled
  3. additiona mixture of Et2O (100 mL) and H2O (100 mL)
  4. additionwas added
  5. customThe aq layer was separated
  6. extractionextracted with Et2O (3×50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customafforded the product

出典と根拠

ORDレコード
ord-232b8803963f40f0a7456c432aca91f1
出典データセット
uspto-grants-2011_08
特許番号
US07999107B2

関連ノート

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