Potassium Carbonate → Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

HRID 1630965Notes

Reaction equation

HRID 1630965 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][O:13][CH2:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

Product 1

HCID 58554139Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (40.0 g, 154 mmol), o-tolylboronic acid (23.1 g, 170 mmol), K2CO3 (106.7 g; 772 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.8 g; 1.54 mmol) was prepared in toluene (200 mL) and water (200 mL) and degassed with N2. The reaction mixture was heated at reflux for 1 hour, and then filtered through a pad of Celite and extracted with EtOAc (1 L). The organic layer was washed with a saturated aqueous solution of NaHCO3 (250 mL), water (250 mL) and brine (250 mL), dried (MgSO4) and concentrated affording the title compound as a yellow oil used without further purification (41.9 g, quantitative). HPLC (Method A), Rt 5.3 min (purity: 89.4%).

Workup

  1. customwater (200 mL) and degassed with N2
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. filtrationfiltered through a pad of Celite
  5. extractionextracted with EtOAc (1 L)
  6. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (250 mL), water (250 mL) and brine (250 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56d7491c0e23422d85bd50810afc54bb
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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