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

HRID 494861ノート

反応式

HRID 494861 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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,

出典と根拠

ORDレコード
ord-91069ddf929c496e9daf055487daa4a3
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

反応ノート

読み込み中…