Sodium Carbonate → Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 2053052노트

반응식

HRID 2053052 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6](Br)[CH:5]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])O1.C(=O)([O-])[O-].[Na+].[Na+].N1C=CN=N1>C(OCC)(=O)C.O.C(O)CC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:5]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 7018022Methyl 3-bromo-4-fluorobenzoateHCID 178418936HCID 178418936, 화합물

생성물 1

HCID 53218663Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

시약·촉매·용매 4

HCID 962Water용매HCID 10311-Propanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2 g (8.45 mmol) of methyl-3-bromo-4-fluorobenzoate in 28 Ml of toluene at RT was added 0.49 g (0.42 mmol) of tetrakis(triphenyl phosphine)palladium(0), 1.95 g (8.9 mmol) of 2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol, 5.1 Ml (10.15 mmol) of 2M aqueous sodium carbonate solution and 14 Ml of n-propanol. The reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled and diluted with ethyl acetate and water. The organic fraction was separated and washed with saturated NaCl solution (brine), dried over MgSO4, filtered and the filtrate was concentrated to an oil which was purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2:acetone) to give the title compound. Mass Spectrum (ESI) m/e (M+1): 247.0.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. customThe organic fraction was separated
  5. washwashed with saturated NaCl solution (brine)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to an oil which
  9. customwas purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2

출처 및 근거

ORD 기록
ord-9aa6d8e99660413f8a7d1a6216a31d26
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326726B2

반응 노트

불러오는 중…