Cesium carbonate → HCID 18457813, compound

HRID 747567Notes

Reaction equation

HRID 747567 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH3:12][O: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.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>[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:10]([CH3:11])=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6216403-Iodo-4-methylbenzoic acidHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 18457813HCID 18457813, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Iodo-4-methylbenzoic acid (8.7 g, 33.3 mmol), (4-methoxycarbonylphenyl)boronic acid (6.0 g, 33.3 mmol), caesium carbonate (1 0.8 g, 33.3 mmol) and tetrakis(triphenylphosphine)palladium (1.92 g, 1.∂mmol) in DME (120 ml) were heated at 90° C. for 6 h. The cooled reaction mixture was filtered and the residue washed with DME. The combined filtrate and washings were absorbed onto silica and chromatographed on a silica flash column eluting with DCM/ethanol/ammonia (40:8:1 then 30:8:1). The product fractions were reduced to dryness under vacuum to give 4′-(methoxycarbonyl)-6-methyl-1,1′-biphenyl-3-carboxylic acid (2.28 g, 25%). LCMS: retention time 3.22 min, [M−H]−269.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe residue washed with DME
  4. customThe combined filtrate and washings were absorbed onto silica
  5. customchromatographed on a silica flash column
  6. washeluting with DCM/ethanol/ammonia (40:8:1

Sources & evidence

ORD record
ord-20c32c253ef645369a544f3ea819bc00
Source dataset
uspto-grants-2008_07
Patent number
US07396843B2

Reaction notes

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