Sodium Acetate → 6-fluoro-3-(3-fluorophenyl)-2-methyl-4H-chromen-4-one

HRID 239632Notes

Reaction equation

HRID 239632 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:7]=1.[C:19]([O-])(=O)[CH3:20].[Na+]>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][C:19]([CH3:20])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[C:8]2=[O:17]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 532346871-(5-Fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone

Product 1

HCID 602090586-fluoro-3-(3-fluorophenyl)-2-methyl-4H-chromen-4-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Intermediate 73 (24 g, 0.096 moles) was taken in a RB flask and to this acetic anhydride (230 ml) and sodium acetate (55.2 g, 0.673 moles) were added and the mixture was refluxed for 12 h. After cooling to RT, the reaction mixture was quenched by the addition of ice cold water. The solid formed was filtered and washed with water. The product was dried under vacuum to afford the title compound as brown solid (26 g, quant. yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.87(dd, J=8.2,3.0 Hz, 1H), 7.48-7.36(m,3H), 7.10-6.99(m, 3H), 2.33(s, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 12 h
  3. customthe reaction mixture was quenched by the addition of ice cold water
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-6d00302d7ace46e7abcccbe8b27e063c
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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