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

HRID 1673253

반응식

HRID 1673253 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-232b8803963f40f0a7456c432aca91f1
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999107B2

연결된 노트

불러오는 중…