Water → Methyl 4-formyl[1,1′-biphenyl]-3-carboxylate

HRID 480081Notes

Reaction equation

HRID 480081 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[CH:5]=1.C([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=O.[C:23]([O-])([O-])=[O:24].[Na+].[Na+].O>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:9]=1[CH:23]=[O:24])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 86586632Methyl 4-formyl[1,1′-biphenyl]-3-carboxylateYield 71.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture if 2.0 g (9.3. mmol.) methyl-3-bromobenzoate, 1.5 g (10.2 mmol.) 4-formylbenzeneboronic acid and 537 mg (0.47 mmol.) tetrakis(triphenylphosphine)-palladium in 14 mL (27.9 mmol.) 2M Na2CO3 and 15 mL dimethoxyethane was heated at 80° C. for 4 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine then dried (MgSO4) and concentrated in vacuo to give an oil. Chromatography on Silica Gel eluting with ethyl acetate/hexanes (1:5) gave 1.6 g 4-formyl-biphenyl-3-carboxylic acid methyl ester as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil

Sources & evidence

ORD record
ord-30a62080966f443ba2fef4bd4591fde1
Source dataset
uspto-grants-2003_11
Patent number
US06649633B2

Reaction notes

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