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

HRID 494818

反応式

HRID 494818 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
25 °C

実験手順

(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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0da99411b31348cc993256a8b9a5432c
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

関連ノート

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