Ammonium Acetate → HCID 22316662, compound

HRID 396829Notes

Reaction equation

HRID 396829 reaction equation
[C:1]([O:4][CH:5]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[C:17]([F:25])[CH:16]=1)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=O)(=O)[CH3:2].C([O-])(=O)C.[NH4+:30]>C(O)(=O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:30]=[C:1]([CH3:2])[O:4][C:5]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[C:17]([F:25])[CH:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 22316853HCID 22316853, compound

Product 1

HCID 22316662HCID 22316662, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The mixture of 2-acetoxy-1-(4-bromophenyl)-2-[3-fluoro-4-(methylsulfonyl)phenyl]-1-ethanone (743.7 mg, 1.733 mmol) and ammonium acetate (333.9 mg, 4.333 mmol) in acetic acid (15 mL) was heated at reflux temperature for 2.5 hours, and cooled down to room temperature. The mixture was evaporated, diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 solution (100 mL×2), water (50 mL), brine (50 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2) to provide the subtitle compound (447.1 mg, 63% yield) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2.5 hours
  3. customThe mixture was evaporated
  4. additiondiluted with ethyl acetate (100 mL)
  5. washwashed with saturated NaHCO3 solution (100 mL×2), water (50 mL), brine (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record
ord-464d965ce10943ec84a4c57f31550818
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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