(1,1'-Biphenyl)-2-ol → 1-(2-Fluoroethoxy)-2-phenylbenzene

HRID 1086010

反応式

HRID 1086010 の反応式
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:21][CH2:22][F:23])(=O)=O>CN(C)C=O>[F:23][CH2:22][CH2:21][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 24758Sodium hydrideHCID 680342-Fluoroethyl methanesulfonate

生成物 1

HCID 156713901-(2-Fluoroethoxy)-2-phenylbenzene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a suspension of sodium hydride (60 % oil dispersion; 4.0 g) in N,N-dimethylformamide (100 ml), 2-phenylphenol (17.0 g) was added at a temperature of 0 to 5° C., and the resultant mixture was stirred at room temperature for 1 hour. 2-Fluoroethyl methanesulfonate (14.2 g) was added thereto. The resulting mixture was heated to 90° C., followed by stirring for 5 minutes. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The extract was washed with aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent, toluene) to give 1-(2-fluoroethoxy)-2-phenylbenzene (Compound No. 20) (16.4 g). nD24.8 1.5796.

後処理

  1. additionwas added at a temperature of 0 to 5° C.
  2. additionThe reaction mixture was poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous potassium carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent, toluene)

出典と根拠

ORDレコード
ord-00740c94dc8a4bf7910ad7562c902468
出典データセット
uspto-grants-1991_04
特許番号
US05012004

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