Acetic Anhydride → 6-fluoro-2-methyl-3-phenyl-4H-chromen-4-one

HRID 1476182Notes

Reaction equation

HRID 1476182 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[C:18](OC(=O)C)(=O)[CH3:19].C([O-])(=O)C.[Na+]>>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:17][C:18]([CH3:19])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]2=[O:16]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 27785851-(5-Fluoro-2-hydroxyphenyl)-2-phenylethanone

Product 1

HCID 602090566-fluoro-2-methyl-3-phenyl-4H-chromen-4-oneYield 80%

Procedure

Intermediate 50 (50 g, 0.217 moles) was taken in a RB flask and to this acetic anhydride (424 ml) and sodium acetate (124 g, 1.51 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 colourless solid (44 g, 80% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.87(dd, J=8.3,3.0 Hz, 1H), 7.47-7.35(m,5H), 7.29(m, 2H), 2.32(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-2e7f80c74fbf42069904d0765f701db9
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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