Ethanol → Ethyl 4-phenyl-2-chlorobenzoate

HRID 1249979Notes

Reaction equation

HRID 1249979 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-1971688cb49f450cb9e01c9fd89c3097
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

Loading…