Acetic Anhydride → HCID 178471853, compound

HRID 377277Notes

Reaction equation

HRID 377277 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:16])[C:3]=1[CH3:17].[C:18](OC(=O)C)(=O)[CH3:19].CO[CH:27](OC)[N:28]([CH3:30])C>C(Cl)Cl>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8](=[CH:30][NH:28][CH:27]2[CH2:19][CH2:18]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:16])[C:3]=1[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 78373Dimethylformamide dimethyl acetalHCID 54193098Ethyl 4-bromo-2-fluoro-3-methyl-β-oxobenzenepropanoate

Product 1

HCID 178471853HCID 178471853, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 14 ml of methylene chloride was dissolved 0.70 g of ethyl 4-bromo-2-fluoro-3-methyl-benzoylacetate, followed by adding thereto 0.29 g of acetic anhydride and 0.33 g of N,N-dimethylformamide dimethyl acetal, and the resulting mixture was stirred at room temperature for 2 hours and then distilled under reduced pressure to remove the solvent. The resulting residue was dissolved in 10 ml of ethanol, followed by adding thereto 0.16 g of cyclopropylamine. The resulting mixture was stirred at room temperature for 12 hours and the crystals precipitated were collected by filtration to obtain 0.72 g of colorless ethyl 2-(4-bromo-2-fluoro-3-methylbenzoyl)-3-cyclopropylaminoacrylate.

Workup

  1. additionby adding
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe resulting residue was dissolved in 10 ml of ethanol
  5. additionby adding
  6. customthe crystals precipitated
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4fe3d11e778f4264b45d93e5dc78adfd
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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