Potassium Iodide → 4-(Benzyloxy)-2-fluorobenzonitrile

HRID 886492노트

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HRID 886492 반응식
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[I-].[K+]>CC(C)=O.O>[CH2:17]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

생성물 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrile수율 90%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

A solution of 2-fluoro-4-hydroxy-benzonitrile (80 g, 0.58 mol), potassium carbonate (162 g, 1.17 mol) and benzyl bromide (76.4 mL, 0.64 mol) and potassium iodide (9.6 g, 0.058 mol) in acetone (600 mL) was stirred at RT and a significant exothermic reaction was observed. Stirring continued for 18 h without cooling. Reaction progress was monitored by TLC analysis. The reaction mixture was diluted with H2O (600 mL) and extracted with EtOAc (500 mL×2). The combined organic extracts were washed with saturated aqueous NaCl solution (500 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was triturated in cyclohexane (300 mL) and the crystalline solid was filtered off and washed to afford 4-Benzyloxy-2-fluoro-benzonitrile (118.2 g, 90%). 1H NMR (400 MHz, CDCl3): 7.51 (1H, dd, J=8.70, 7.48 Hz), 7.40 (5H, m), 6.86-6.76 (2H, m), 5.11 (2H, s).

후처리

  1. customa significant exothermic reaction
  2. temperaturewithout cooling
  3. customReaction progress
  4. extractionextracted with EtOAc (500 mL×2)
  5. washThe combined organic extracts were washed with saturated aqueous NaCl solution (500 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue was triturated in cyclohexane (300 mL)
  10. filtrationthe crystalline solid was filtered off
  11. washwashed

출처 및 근거

ORD 기록
ord-365df0038242448eae516e4fac642489
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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