Iodine → (4-Fluorophenyl)(4-hydroxy-3-iodophenyl)methanone

HRID 494818

반응식

HRID 494818 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[I-:17].[K+].II>[OH-].[NH4+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([I:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 807IodineHCID 4875Potassium IodideHCID 1176664-Fluoro-4'-hydroxybenzophenone

생성물 1

HCID 11382275(4-Fluorophenyl)(4-hydroxy-3-iodophenyl)methanone수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 14923Ammonium Hydroxide용매

반응 조건

온도
25 °C

실험 절차

(4-Fluorophenyl)(4-hydroxyphenyl)methanone (20.0 g, 92.5 mmol) in concentrated ammonium hydroxide (770 mL) was allowed to stir at 25° C. for 15 minutes and then treated with potassium iodide (74.79 g, 450.5 mmol) and iodine (23.48 g, 92.5 mmol) in water (185 mL). The reaction mixture was allowed to stir at 25° C. for 18 hours and then filtered. The precipitate was dissolved in ethyl acetate, washed with water and brine, dried, filtered and the filtrate concentrated under reduced pressure to provide the title compound as a pale green solid (23.4 g, 74% yield). 1HNMR (300 MHZ, CD3OD) δ 6.91 (d, 1H, J=8.9 Hz), 7.26 (t, 2H), 7.64 (d, 1H, J=8.9 Hz), 7.78 (t, 2H), 8.17 (s, 1H; MS (DCI) m/z 342.9 (M+H)+, 360 (M+NH4)+.

후처리

  1. stirringto stir at 25° C. for 18 hours
  2. filtrationfiltered
  3. dissolutionThe precipitate was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0da99411b31348cc993256a8b9a5432c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

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