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

HRID 494818

Reaction equation

HRID 494818 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

(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)+.

Workup

  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

Sources & evidence

ORD record
ord-0da99411b31348cc993256a8b9a5432c
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Linked notes

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