Sodium Acetate → HCID 53234359, compound

HRID 1476149Notes

Reaction equation

HRID 1476149 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][C:13]([F:16])=[CH:12][CH:11]=2)[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][C:13]([F:16])=[CH:12][CH:11]=1)[C:8]2=[O:17]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 53234358HCID 53234358, compound

Product 1

HCID 53234359HCID 53234359, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Intermediate 6 (6.1 g, 19.73 mmoles) was taken in a RB flask and to this acetic anhydride (40 ml) and sodium acetate (11.3 g, 137.75 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 (4.1 g, 63% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 8.35(d, J=1.9Hz, 1H), 7.77(dd, J=8.8, 1.9Hz, 1H), 7.37(d, J=8.9Hz, 1H), 7.27(t, J=5.7Hz, 2H), 7.17(t, J=8.6Hz, 2H), 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-51be0cebc7d4466184a19e05bcab5fd9
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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