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

HRID 42396

反応式

HRID 42396 の反応式
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

参加物

4

反応物 3

HCID 80561,4-DibromobutaneHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 178418306HCID 178418306、化合物

生成物 1

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

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-04769ea0cd3040258ed0ef6b88653b08
出典データセット
uspto-grants-2013_09
特許番号
US08535974B2

関連ノート

読み込み中…