Hydrochloric Acid → 1-[4-(4-Chlorophenoxy)-2-propylphenyl]ethanone

HRID 1172811

Reaction equation

HRID 1172811 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH2:21][CH2:22][CH3:23])(=O)=O.[CH:26]([O:28]CCCC)=[CH2:27].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([C:26](=[O:28])[CH3:27])=[C:8]([CH2:21][CH2:22][CH3:23])[CH:9]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 574201394-(4-Chlorophenoxy)-2-propylphenyl trifluoromethanesulfonate

Product 1

HCID 574201401-[4-(4-Chlorophenoxy)-2-propylphenyl]ethanone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Step 6 (2.0 g, 5.0 mmol), n-butyl vinyl ether (25 mmol), triethylamine (0.83 mL, 6.0 mmol), palladium acetate (0.125 mmol) and 1,3-bis(diphenylphosphino)propane (51.5 mg, 0.125 mmol) in DMF (25 mL) was heated at 80° C. under nitrogen for 4 h. The reaction mixture was poured into 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and concentrated. The residue was purified by chromatography on silica gel to afford the title product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-63abfcd3df294a0d9084bf9e7ce43386
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Linked notes

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