Dichloromethane → 1-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

HRID 494861노트

반응식

HRID 494861 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:9](=[O:11])[CH3:10])[CH:17]=2)=[CH:3][CH:4]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 108944-IodophenolHCID 27343103-Acetylphenylboronic acid

생성물 1

HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone수율 95%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

4-Iodophenol (5.39 g, 24.5 mmol) and 3-acetylphenylboronic acid (4.42 g, 26.95 mmol) were mixed in N,N-dimethylformamide (15 mL) and treated with 1.0 M aqueous Na2CO3 (75 mL) and palladium (II) acetate (110 mg, 0.49 mmol). The suspension was heated at 55° C. for one hour and then brought to room temperature. CH2Cl2 (100 mL) was added to the mixture which was then filtered. The aqueous layer of the filtrate was extracted with CH2Cl2 and the combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine, then dried (Na2SO4), concentrated, and chromatographed through silica with a 33 to 100% gradient of hexanes/CH2Cl2 followed by a gradient of 0 to 3% EtOAc/CH2Cl2. Impure fractions were combined, concentrated, and rechromatographed as before, twice, to provide the title compound as an oil which slowly crystallized to a white solid upon standing (˜95% yield). MS (ESI APCI negative ion detection) m/z 211 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.65 (s, 3H), 6.97 (d, 2H), 7.47-7.53 (m, 3H), 7.74 (ddd, 1H), 7.88 (ddd, 1H), 8.13 (dd, 1H).

후처리

  1. custombrought to room temperature
  2. filtrationwas then filtered
  3. extractionThe aqueous layer of the filtrate was extracted with CH2Cl2
  4. washthe combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed through silica with a 33 to 100% gradient of hexanes/CH2Cl2
  8. concentrationconcentrated
  9. customrechromatographed as before, twice,

출처 및 근거

ORD 기록
ord-91069ddf929c496e9daf055487daa4a3
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

반응 노트

불러오는 중…