Dimethylformamide → 4-(4-Chlorophenoxy)-2-propylbenzaldehyde

HRID 1172817Notes

Reaction equation

HRID 1172817 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.C([SiH](CCCCCCCC)CCCCCCCC)CCCCCCC.C(N(CC)CC)C.C1(PC2C=CC=CC=2)C=CC=CC=1.CN([CH:74]=[O:75])C>C(OCC)(=O)C.O.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]([CH:74]=[O:75])=[C:8]([CH2:21][CH2:22][CH3:23])[CH:9]=2)=[CH:15][CH:16]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 87780Trioctylsilane, 95%HCID 574201394-(4-Chlorophenoxy)-2-propylphenyl trifluoromethanesulfonate

Product 1

HCID 574201434-(4-Chlorophenoxy)-2-propylbenzaldehyde

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the triflate from Step 6 of Example 1 (3.98 g, 10 mmol), trioctylsilane (6.7 mL, 15 mmol), triethyl amine (7.0 mL, 25 mmol), palladium acetate (0.22 g, 0.5 mmol) and diphenylphosphine (0.21 g, 0.5 mmol) in DMF (60 mL) was stirred at 80° C. under an atmosphere of carbon monoxide (50 psi) for 5 h. The reaction was then diluted with ethyl acetate and water. The organic layer was washed with water and concentrated. The residue was purified by chromatography on silica gel to give the title product.

Workup

  1. washThe organic layer was washed with water
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3b6927da955b4e40becf93811e4e50c6
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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