Potassium Carbonate → 2-Bromo-1-(4-fluoro-3-methylphenyl)ethanone

HRID 2402733Notes

Reaction equation

HRID 2402733 reaction equation
[Br:1][CH2:2][C:3]([O:5]C)=O.C1(C2NC=C([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([CH3:25])[CH:19]=3)N=2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][CH2:2][C:3]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([CH3:25])[CH:19]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178422928HCID 178422928, compound

Product 1

HCID 109773012-Bromo-1-(4-fluoro-3-methylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.38 mL methyl bromoacetate was added to 940 mg 2-cyclohexyl-4-(4-fluoro-3-methyl-phenyl)-1H-imidazole and 1.52 g potassium carbonate in 10 mL DMF. The reaction was stirred over night at RT and evaporated. Methanol and 1 mol/L sodiumhydroxide solution was added and the mixture was stirred 2 h at RT. The solvent was removed. The residue was dissolved in water and acidified with 1 mol/L HCL solution. The precipitate was filtered and dried to give 700 mg desired product. Rt: 0.92 min (method A), (M+H)+: 317

Workup

  1. customevaporated
  2. additionMethanol and 1 mol/L sodiumhydroxide solution was added
  3. stirringthe mixture was stirred 2 h at RT
  4. customThe solvent was removed
  5. dissolutionThe residue was dissolved in water
  6. filtrationThe precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-c80e9f630fe040fe9be33419890989d7
Source dataset
uspto-grants-2014_08
Patent number
US08796467B2

Reaction notes

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