Sodium Carbonate → Methyl 2-methyl-[1,1'-biphenyl]-4-carboxylate

HRID 1174968Notes

Reaction equation

HRID 1174968 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[C:6]([CH3:11])[CH:5]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH3:11])[CH:5]=1)=[O:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 53670602Methyl 2-methyl-[1,1'-biphenyl]-4-carboxylateYield 10.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 4-bromo-3-methyl-benzoic acid methyl ester (1.0 g, 4.36 mmol) and phenylboronic acid (0.64 g, 5.24 mmol) in n-PrOH (15 mL) is treated with 2 M Na2CO3 (4.4 mL), and purged with N2 for 10 min, and Pd(PPb3)4 (25 mg, 0.22 mmol) is then added. The reaction is refluxed overnight. Organic solvent is removed in vacuo, the residue is extracted with CH2Cl2 (30 mL), washed with 10% Na2CO3 (30 mL), H2O (30 mL); dried with Na2SO4 and concentrated. Purification of the crude material by chromatography affords the title compound (0.10 g, 10%).

Workup

  1. custompurged with N2 for 10 min
  2. temperatureThe reaction is refluxed overnight
  3. customOrganic solvent is removed in vacuo
  4. extractionthe residue is extracted with CH2Cl2 (30 mL)
  5. washwashed with 10% Na2CO3 (30 mL), H2O (30 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customPurification of the crude material by chromatography

Sources & evidence

ORD record
ord-3ddc5e85fe9d40ccb867501d538f9a63
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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