N-Iodosuccinimide → 4-Acetyl-6-chloro-3-hydroxy-2-iodobenzonitrile

HRID 626834노트

반응식

HRID 626834 반응식
[C:1]([C:4]1[C:11]([OH:12])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([Cl:13])[CH:5]=1)(=[O:3])[CH3:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]([Cl:13])[C:7]([C:8]#[N:9])=[C:10]([I:14])[C:11]=1[OH:12])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 866975254-Acetyl-2-chloro-5-hydroxybenzonitrile

생성물 1

HCID 866975264-Acetyl-6-chloro-3-hydroxy-2-iodobenzonitrile수율 66%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

The 4-acetyl-2-chloro-5-hydroxybenzonitrile (4.9 g, 25 mmol) was dissolved in acetic acid (61.2 mL), and the N-iodosuccinimide (6.8 g, 30 mmol) was added. The reaction was heated to 80° C. and, after heating for 18 hrs, the reaction was concentrated in vacuo to remove the acetic acid. The residue was taken up in ethyl acetate, washed with sodium bicarbonate water, brine, dried over magnesium sulfate and concentrated to give a dark oil. The crude product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-6-chloro-3-hydroxy-2-iodobenzonitrile as a yellow solid (5.3 g, 66%).

후처리

  1. temperatureafter heating for 18 hrs
  2. concentrationthe reaction was concentrated in vacuo
  3. customto remove the acetic acid
  4. washwashed with sodium bicarbonate water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a dark oil
  8. customThe crude product was purified by FCC on silica gel
  9. washeluting hexane

출처 및 근거

ORD 기록
ord-b86fd382a8de4bdc8934cd5ed2c7947b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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