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

HRID 2053052ノート

反応式

HRID 2053052 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 10311-Propanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9aa6d8e99660413f8a7d1a6216a31d26
出典データセット
uspto-grants-2008_02
特許番号
US07326726B2

反応ノート

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