Hydrochloric Acid → 3-Fluoro-4-hydroxy-5-iodobenzonitrile

HRID 263494

반응식

HRID 263494 반응식
[I-:1].[K+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([F:12])[CH:6]=1)#[N:4].CC1C=CC(S(NCl)(=O)=O)=CC=1.Cl>CN(C=O)C.O>[C:3]([C:5]1[CH:10]=[C:9]([I:1])[C:8]([OH:11])=[C:7]([F:12])[CH:6]=1)#[N:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 31388TosylchloramideHCID 27829443-Fluoro-4-hydroxybenzonitrile

생성물 1

HCID 190382723-Fluoro-4-hydroxy-5-iodobenzonitrile수율 55.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

Potassium iodide (7.97 g, 48 mmol) was dissolved in 125 ml of DMF with stirring, and 4-cyano-2-fluorophenol (16a; 5.56 g 48 mmol) and chloramine-T in 75 ml of DMF were added dropwise with stirring. The reaction mixture was poured into 650 ml of water, acidified with 6N HCl, and extracted with ethyl acetate. The organic layer was washed with 10% NaHSO3, water and brine and dried over magnesium sulfate. The organic solution was concentrated in vacuo and the yellow solid residue was treated with 200 ml of 1N NaOH solution, filtered through supercel, and the filtrate was acidified with conc. HCl solution. The solid product was filtered, dried, dissolved in ether, and the organic layer was dried over magnesium sulfate. The organic solution was concentrated in vacuo and the residue was recrystallized from ethylene chloride to afford 5.93 g (55.6%) of the title compounds.

후처리

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 10% NaHSO3, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic solution was concentrated in vacuo
  6. additionthe yellow solid residue was treated with 200 ml of 1N NaOH solution
  7. filtrationfiltered through supercel
  8. filtrationThe solid product was filtered
  9. customdried
  10. dissolutiondissolved in ether
  11. dry with materialthe organic layer was dried over magnesium sulfate
  12. concentrationThe organic solution was concentrated in vacuo
  13. customthe residue was recrystallized from ethylene chloride

출처 및 근거

ORD 기록
ord-a757a5b3453d4d1282436b46e3c69f2d
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643929

연결된 노트

불러오는 중…