Potassium Phosphate, Tribasic → Methyl 2,6-dimethoxybiphenyl-4-carboxylate

HRID 1096976Notes

Reaction equation

HRID 1096976 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:14][CH3:15].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC#N>[CH3:15][O:14][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[C:11]([O:12][CH3:13])[C:2]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 117713Methyl 4-bromo-3,5-dimethoxybenzoate

Product 1

HCID 57930909Methyl 2,6-dimethoxybiphenyl-4-carboxylate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

PdCl2(dppf) (14.8 g) was added to a CH3CN (900 mL) solution of methyl 4-bromo-3,5-dimethoxybenzoate (25.0 g), phenylboronic acid (22.2 g), Bu4NBr (5.86 g) and K3PO4 (77.2 g), and stirred under heat for 14 hours. This was filtered through Celite, and the filtrate was concentrated and purified through column chromatography to obtain the title compound as a colorless solid.

Workup

  1. temperatureunder heat for 14 hours
  2. filtrationThis was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified through column chromatography

Sources & evidence

ORD record
ord-d3f5b8e3929b4e0d9c1c794ccf02fcd9
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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