Phenacyl bromide → HCID 86725347, compound

HRID 925240Notes

Reaction equation

HRID 925240 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([OH:17])[C:14]([I:16])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:6][CH2:7][C:8]2[CH:15]=[C:14]([I:16])[C:13]([O:17][CH2:21][C:22](=[O:23])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:12][C:9]=2[CH2:10][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 86725348HCID 86725348, compound

Product 1

HCID 86725347HCID 86725347, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dry acetone (6 ml) was added to a flask containing the product from step (a) (0.528 g, 1.3 mmol). To this was added 2-Bromo-1-phenyl-ethanone (0.327 g, 1.6 mmol, 1.2 eq) and potassium carbonate (0.378 g, 2.7 mmol, 2.0 eq). The reaction mixture was allowed to stir for 16 hours at room temperature. The acetone was removed under vacuum and the solid was dissolved in dichloromethane, washed with 4N HCl, and brine. Purification by silica-gel chromatography (gradient elution: 0-100% EtOAc in hexanes) gave the sub-title compound as a white solid (552 mg). MS: ESI (positive): 504 (M+H).

Workup

  1. customThe acetone was removed under vacuum
  2. dissolutionthe solid was dissolved in dichloromethane
  3. washwashed with 4N HCl, and brine
  4. customPurification
  5. washby silica-gel chromatography (gradient elution: 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b39f718ccaeb4a50b8541e495da9be38
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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