Water → 2-Phenylterephthalic acid mono methyl ester

HRID 2121120Notes

Reaction equation

HRID 2121120 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC[O:25][C:26]1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl.[C]=[O:41].O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:26]([OH:25])=[O:41])=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 175534Tesmilifene HydrochlorideHCID 54332024Methyl 5-bromo-[1,1'-biphenyl]-2-carboxylateHCID 178418416HCID 178418416, compound

Product 1

HCID 857324742-Phenylterephthalic acid mono methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-2-phenylbenzoic acid methyl ester (1.0 equivalent), Pd(OAc)2 (0.05 equivalent) and DPPE (1.0 equivalent) is heated in DMF to 65° C. under 4 atm. of carbon monoxide until TLC analysis indicates that the reaction is complete. The reaction mixture is poured into water and extracted with ethyl acetate which is dried and evaporated. The product is purified by chromatography on silica gel.

Workup

  1. extractionextracted with ethyl acetate which
  2. customis dried
  3. customevaporated
  4. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c6055bbfac974b40aea7f7b5b6b3a25d
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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