Diethylene Glycol → 4-Ethyl-2-fluoro-1,1'-biphenyl

HRID 2309302

反応式

HRID 2309302 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([F:16])[CH:5]=1)(=O)[CH3:2].O.NN.[OH-].[K+].C(O)COCCO>C1(C)C(C)=CC=CC=1>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:6]([F:16])[CH:5]=1)[CH3:2]

参加物

6

反応物 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 64519181-(2-Fluoro(1,1'-biphenyl)-4-yl)ethan-1-one

生成物 1

HCID 14903264-Ethyl-2-fluoro-1,1'-biphenyl収率 68%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

4-Acetyl-2-fluorobiphenyl (150 gram), 99% hydrazine hydrate (150 ml), potassium hydroxide (105 gram), digol (900 ml) and xylene (150 ml) were heated at 125° C. for 16 hours with stirring, after which the xylene and excess hydrazine hydrate were distilled until the internal temperature reached 165° C. The mixture was heated under reflux for three hours, cooled to 40° and poured into 5 liters of water. The product was extracted with petroleum ether (bp 60°-80°, 2×2 liter), the extract washed with water, dried over anhydrous sodium sulphate and evaporated. 4-Ethyl-2-fluorobiphenyl (95 gram, 68% theory) formed a colourless oil bp 130°/0.8 mm. Other 4-Alkyl-2-fluorobiphenyls were prepared by reaction of 2-fluoro-4-biphenylyl magnesium bromides with n-alkyl bromides and were colourless oils with the following properties listed in Table 5.

後処理

  1. distillationafter which the xylene and excess hydrazine hydrate were distilled until the internal temperature
  2. customreached 165° C
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for three hours
  5. temperaturecooled to 40°
  6. additionpoured into 5 liters of water
  7. extractionThe product was extracted with petroleum ether (bp 60°-80°, 2×2 liter)
  8. washthe extract washed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. customevaporated

出典と根拠

ORDレコード
ord-36378cc353d045b3b81aa262e2376455
出典データセット
uspto-grants-1987_09
特許番号
US04695131

関連ノート

読み込み中…