Sodium Acetate → 6-bromo-2-methyl-3-o-tolyl-4H-chromen-4-one

HRID 1476151Notes

Reaction equation

HRID 1476151 reaction equation
[Br: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]=[CH:12][C:11]=2[CH3:16])[CH:7]=1.[C:19]([O-])(=O)[CH3:20].[Na+]>C(OC(=O)C)(=O)C>[Br: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]=[CH:12][C:11]=1[CH3:16])[C:8]2=[O:17]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 532343631-(5-Bromo-2-hydroxyphenyl)-2-o-tolylethanone

Product 1

HCID 532343646-bromo-2-methyl-3-o-tolyl-4H-chromen-4-oneYield 33.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Intermediate 11 (5.5 g, 16.38 mmoles) was taken in a RB flask and to this acetic anhydride (50 ml) and sodium acetate (9.40 g, 114.69 mmoles) 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 white solid (1.8 g, 30% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 8.35(d, J=1.7Hz, 1H), 7.75(d, J=6.7 Hz, 1H), 7.37(d, J=8.8Hz, 1H), 7.35-7.26(m, 3H), 7.09(d, J=6.9Hz, 1H), 2.20(s, 3H).2.15(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-4105b358be264c44b0168dac72576e22
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

Loading…