Water → Methyl 2',4'-dimethoxy-2-methylbiphenyl-4-carboxylate

HRID 219788Notes

Reaction equation

HRID 219788 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[CH3:12].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.CCOC(C)=O.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>[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343412,4-Dimethoxybenzeneboronic acidHCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 67528466Methyl 2',4'-dimethoxy-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-bromo-3-methylbenzoate obtained in step 1 (3 g; 13.10 mmol), 2,4-dimethoxyphenylboronic acid (2.62 g; 14.4 mmol), potassium carbonate (9.05 g; 65.48 mmol), tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol) were taken in toluene (15 mL) and water (15 mL) under N2 atmosphere. The reaction mixture was purged with vacuum and degassed with N2 and then refluxed for 6 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (200 mL). The filtrate was concentrated to afford a brown oil which was taken in EtOAc (300 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (100 mL), water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil that was used without further purification (3.7 g, 98%). HPLC (Method A) Rt 4.74 min (Purity: 59.9%).

Workup

  1. customThe reaction mixture was purged with vacuum
  2. customdegassed with N2
  3. temperaturerefluxed for 6 hours
  4. filtrationfiltered over a pad of celite
  5. washwashed with toluene (200 mL)
  6. concentrationThe filtrate was concentrated
  7. customto afford a brown oil which
  8. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 solution (100 mL), water (100 mL) and brine (100 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-49c32c58773f49f493f6706f65d9490b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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