1,4-Dibromobutane → 2-(3-(4-Bromobutyl)phenyl)-1,3-dioxolane

HRID 42396

반응식

HRID 42396 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 3

HCID 80561,4-DibromobutaneHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 580284682-(3-(4-Bromobutyl)phenyl)-1,3-dioxolane

반응 조건

온도
-20 °C

실험 절차

To a clean and dry 2000 ml round bottom flask equipped with a 500 ml addition funnel, low temperature thermometer and magnetic stir bar was transferred anhydrous tetrahydrofuran (800.0 ml) under nitrogen. 2-(3-bromophenyl)-1,3-dioxolane (33.0 ml, 0.2183 mol) was added to this flask by syringe. The reaction vessel was placed into a dry ice/acetone bath until a temperature of <−65° was achieved. The reaction mixture was then allowed to stir for 45 minutes at a stirring speed of 550 rpm in order to verify the integrity of the stirring apparatus at this temperature. Tert-butyllithium solution (257.0 ml, 0.4690 mol) was transferred to the addition funnel by cannula, then added drop wise to the reaction never allowing the temperature to rise above −65° C. Following addition, the reaction was allowed to stir for a period of 30 minutes. The vessel was then removed from the dry ice/acetone bath and allowed to warm to a temperature of −20° C. The vessel was then again placed into the dry ice/acetone bath until a temperature of <−65° was achieved. 1,4-dibromobutane (103.5 ml, 0.8740 mol) was added to the reaction dropwise via syringe, maintaining the current temperature. The reaction was allowed to stir for 30 minutes at this temperature following addition. The reaction was slowly warmed to room temperature over the following 12 hours. After warming, the reaction was quenched by the addition of isopropanol (20.0 ml) via syringe.

후처리

  1. customTo a clean and dry 2000 ml round bottom flask
  2. customequipped with a 500 ml addition funnel
  3. customThe reaction vessel was placed into a dry ice/acetone bath until a temperature of <−65°
  4. additionadded drop
  5. customwise to the reaction
  6. customto rise above −65° C
  7. additionaddition
  8. stirringto stir for a period of 30 minutes
  9. customThe vessel was then removed from the dry ice/acetone bath
  10. customwas then again placed into the dry ice/acetone bath until a temperature of <−65°
  11. temperaturemaintaining the current temperature
  12. stirringto stir for 30 minutes at this temperature
  13. additionaddition
  14. temperatureThe reaction was slowly warmed to room temperature over the following 12 hours
  15. temperatureAfter warming
  16. customthe reaction was quenched by the addition of isopropanol (20.0 ml) via syringe

출처 및 근거

ORD 기록
ord-04769ea0cd3040258ed0ef6b88653b08
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08535974B2

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