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

HRID 2309302

반응식

HRID 2309302 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 14903264-Ethyl-2-fluoro-1,1'-biphenyl수율 68%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-36378cc353d045b3b81aa262e2376455
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695131

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