Acetic Acid → 5,7-Difluoro-2-(4-hydroxyphenyl)-4H-chromen-4-one

HRID 884668Notes

Reaction equation

HRID 884668 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[CH:5]=[C:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)[O:7]2.I.C(O)(=O)C>O>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[CH:5]=[C:6]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[O:7]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24841Hydrogen iodideHCID 116378225,7-Difluoro-2-(4-methoxyphenyl)-4H-chromen-4-one

Product 1

HCID 116519765,7-Difluoro-2-(4-hydroxyphenyl)-4H-chromen-4-oneYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 5,7-Difluoro-2-(4-methoxyphenyl)-4H-chromen-4-one (0.425 g, 1.47 mmol), hydroiodic acid (10 mL) and acetic acid (5 mL). The reaction mixture was heated 110° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with water. The precipitate was filtered off, washed with water and dried to give the title compound (220 mg, 54%). Selected data for the title compound: MS (ES) m/z: 275.10 (M+1); 19F-NMR (DMSO-d6): δ −106.2, −113.4.

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5e806ca5705c45b48ac562a13a64439a
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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