Cesium carbonate → 3-Methyl 6-methyl[1,1′-biphenyl]-3,4′-dicarboxylate

HRID 1678461Notes

Reaction equation

HRID 1678461 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6](Br)[CH:5]=1.[OH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:19]2[CH:20]=[CH:21][C:16]([C:14]([OH:15])=[O:13])=[CH:17][CH:18]=2)[C:7]([CH3:10])=[CH:8][CH:9]=1)=[O:12]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3121834-Carboxyphenylboronic AcidHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 218337563-Methyl 6-methyl[1,1′-biphenyl]-3,4′-dicarboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromo-4-methyl-benzoic acid methyl ester (3 g), 4-hydroxycarbonyl-phenyl boronic acid (2.21 g), cesium carbonate (4.26 g) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (75 ml) was heated to reflux for 18 h. The cooled reaction was then evaporated to dryness and the residue purified on silica gel. Elution with dichloromethane:ethanol:0.880 ammonia; 800:8:1 to 100:8:1 gave a yellow crystalline solid (3.4 g)

Workup

  1. temperatureto reflux for 18 h
  2. customThe cooled reaction
  3. customwas then evaporated to dryness
  4. customthe residue purified on silica gel
  5. washElution with dichloromethane

Sources & evidence

ORD record
ord-4d783a02099e499795062113b560c228
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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