Ethanol → Ethyl 4-phenyl-2-chlorobenzoate

HRID 1870444Notes

Reaction equation

HRID 1870444 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10](OS(C(F)(F)F)(=O)=O)=[C:9]([Cl:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:51]([OH:53])[CH3:52].C(N(CC)CC)C.CN(C)[CH:63]=[O:64]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCC.O>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:63]([O:53][CH2:51][CH3:52])=[O:64])=[C:9]([Cl:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 702EthanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 180010793-Chlorobiphenyl-4-yl trifluoromethanesulfonate

Product 1

HCID 18001012Ethyl 4-phenyl-2-chlorobenzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-phenyl-2-chloro-1-trifluoromethylsulfonyloxybenzene (35 g) in dimethylformamide (300 ml) are added palladium acetate (1.17 g), 1,3-bis(diphenylphosphino)propane (4.29 g), ethanol (91.5 ml) and triethylamine (29.0 ml) under carbon monooxide atmosphere, and the mixture is heated with stirring at 80-90° C. for 6 hours. To the reaction solution is added water, and further added a small amount of n-hexane. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed with water, dried, and the residue is purified by silica gel column chromatography (solvent; n-hexane →ethyl acetate:n-hexane=1:100) to give ethyl 4-phenyl-2-chlorobenzoate (20.9 g) as colorless oil.

Workup

  1. temperaturethe mixture is heated
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe ethyl acetate layer is washed with water
  4. customdried
  5. customthe residue is purified by silica gel column chromatography (solvent; n-hexane →ethyl acetate:n-hexane=1:100)

Sources & evidence

ORD record
ord-ac17980b04a943abb4a2783215c5e1a9
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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