Hydrochloric Acid → HCID 66777466, compound

HRID 2091054Notes

Reaction equation

HRID 2091054 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.Br[CH2:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:16]1([C:14]([C:13]2[O:11][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=3[C:8]=2[CH3:9])=[O:15])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenolHCID 111600272-Bromo-1-cyclohexylethanone

Product 1

HCID 66777466HCID 66777466, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5′-fluoro-2′-hydroxyacetophenone (5.00 g), 2-bromo-1-cyclohexylethanone (7.98 g) synthesized above and N,N-dimethylformamide (50 mL) was added potassium carbonate (13.4 g), and the mixture was stirred at room temperature overnight. 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 purified by silica gel column chromatography (0-20% ethyl acetate/hexane) to give the title object compound (5.38 g, 64%) as a pale-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. customThe residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1de718e6b381467ea3fc01886d7422c0
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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