Dibromomethane → 1-Bromo-2-(4-chlorophenyl)-2-cyano-4-phenoxybutane

HRID 260343

반응식

HRID 260343 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]#[N:12])=[CH:6][CH:5]=1.[Br:22][CH2:23]Br>CN(C=O)C>[Br:22][CH2:23][C:10]([C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1)([C:11]#[N:12])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 3024DibromomethaneHCID 24758Sodium hydrideHCID 224014342-(4-Chlorophenyl)-4-phenoxybutanenitrile

생성물 1

HCID 153346041-Bromo-2-(4-chlorophenyl)-2-cyano-4-phenoxybutane수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a flask was added 6.1 g. (0.127 mole) of a 50% oil dispersion of sodium hydride. After washing the sodium hydride several times with hexane to remove the mineral oil, 50 ml. of dry DMF was added, then a solution of 30 g. (0.11 mole) of 2-(4-chlorophenyl)-4-phenoxybutanenitrile in 25 ml. of dry DMF was added dropwise at 0° C. The reaction was stirred and allowed to warm to room temperature over 1.5 hours, then 21.2 g. (0.127 mole) of dibromomethane was added dropwise at 15° C. Upon completion of the addition, the reaction was stirred and heated to 50° C. and was complete in three hours. The reaction mixture was cooled to room temperature, diluted with 300 ml. of water, and then extracted three times with 100 ml. portions of methylene chloride. The combined extracts were washed with dilute hydrochloric acid and water, then dried using sodium sulfate. Upon removal of the solvent, 31 g. of 1-bromo-2-(4-chlorophenyl)-2-cyano-4-phenoxybutane was obtained (77% yield).

후처리

  1. additionTo a flask was added 6.1 g
  2. washAfter washing the sodium hydride several times with hexane
  3. customto remove the mineral oil, 50 ml
  4. additionof dry DMF was added
  5. additionUpon completion of the addition
  6. stirringthe reaction was stirred
  7. temperatureheated to 50° C.
  8. temperatureThe reaction mixture was cooled to room temperature
  9. additiondiluted with 300 ml
  10. extractionof water, and then extracted three times with 100 ml
  11. washThe combined extracts were washed with dilute hydrochloric acid and water
  12. customdried
  13. customUpon removal of the solvent, 31 g

출처 및 근거

ORD 기록
ord-c47a7f519ea7492da93eda1ced67b7bd
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527816

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