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

HRID 219837Notes

Reaction equation

HRID 219837 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[OH:12].[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>[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.C1(C)C=CC=CC=1>[OH:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

HCID 58554208Methyl 2-hydroxy-2'-methyl-[1,1'-biphenyl]-4-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of methyl 4-bromo-3-hydroxybenzoate (25 g, 0.108 mol) and o-tolylboronic acid (22 g, 0.162 mol) in a toluene (500 mL) water (100 mL) mixture, was added anhydrous potassium carbonate (44 g, 0.324 mol) followed by tetrakis (triphenylphosphine) palladium (0) (6.25 g, 0.054 mol). The reaction mixture was degassed with N2 and heated at 110° C. for 12 h. After cooling to RT, the reaction mixture was filtered through a celite pad that was washed further with ethyl acetate. Combined filtrates were washed with 10% solution of NaHCO3, water and brine solution. The solvents were dried over Na2SO4 and evaporated under vacuum. The residue was purified by chromatography (pet ether/EtOAc as an eluent) to afford the title compound as pale yellow solid (20 g, 77%). 1H NMR (DMSO-d6, 400 MHz) δ 9.85 (1H, s), 7.52 (1H, s), 7.44-7.46 (1H, m), 7.20-7.25 (3H, m), 7.14-7.16 (1H, m), 7.09-7.11 (1H, m), 3.84 (3H, s), 2.09 (3H, s).

Workup

  1. customThe reaction mixture was degassed with N2
  2. temperatureAfter cooling to RT
  3. filtrationthe reaction mixture was filtered through a celite pad that
  4. washwas washed further with ethyl acetate
  5. washCombined filtrates were washed with 10% solution of NaHCO3, water and brine solution
  6. dry with materialThe solvents were dried over Na2SO4
  7. customevaporated under vacuum
  8. customThe residue was purified by chromatography (pet ether/EtOAc as an eluent)

Sources & evidence

ORD record
ord-53aadc0776ad436c87090c4e352a432f
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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