Hydrochloric Acid → Cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methanone

HRID 2091200Notes

Reaction equation

HRID 2091200 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=O)[CH3:12].Br[CH2:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:18]1([C:16]([C:15]2[O:1][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=3[C:11]=2[CH3:12])=[O:17])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2480792'-Hydroxy-5'-nitroacetophenoneHCID 111600272-Bromo-1-cyclohexylethanone

Product 1

HCID 66777339Cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methanoneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2′-hydroxy-5′-nitroacetophenone (5.00 g), 2-bromo-1-cyclohexylethanone (6.79 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (7.63 g), and the mixture was stirred overnight at room temperature. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (4.18 g, 53%) as a yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-b01f661f02134d67bf3f00aad0db0b30
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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