Sodium Carbonate → Methyl 6-methoxy-[1,1'-biphenyl]-3-carboxylate

HRID 423326Notes

Reaction equation

HRID 423326 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Na+].[Na+].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>COCCOC>[CH3:13][O:12][C:11]1[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 611662Methyl 3-bromo-4-methoxybenzoate

Product 1

HCID 11010121Methyl 6-methoxy-[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-bromo-4-(methyloxy)benzoate (245 mg, 1 mmol, commercially available) was dissolved in DME: 2N Na2CO3 (2:1, 18 ml) and then phenyl boronic acid (244 mg) and tetrakistriphenylphosphine palladium(0) (58 mg) were added. The reaction was heated to 80° C. and then left to cool over the weekend. Added EtOAc and water, the organics were separated, dried and evaporated to give a black gum. Purification by flash chromatography afforded the title compound (194 mg) as a gum. δH (d6-DMSO, 400 MHz) 3.83 (3H, s), 3.85 (3H, s), 7.24 (1H, d), 7.33-7.50 (5H, m), 7.83 (1H, d), 7.97 (1H, dd). MS (ES): C15H14O3 requires 242; found 243 (MH+).

Workup

  1. waitleft
  2. temperatureto cool over the weekend
  3. customAdded EtOAc and water, the organics were separated
  4. customdried
  5. customevaporated
  6. customto give a black gum
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-9fd2595a09c84a979525da6427509836
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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