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Sodium Carbonate → Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate

HRID 1249970
Notes
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Reaction equation

HRID 1249970 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([O:18][CH3:19])[CH:5]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1OB(O)O.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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.O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH3:21])=[C:6]([O:18][CH3:19])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 106151343-Methoxy-4-trifluoromethylsulfonyloxybenzoic acid methyl esterHCID 13862916Tolylboric acid

Product 1

HCID 53941402Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylateYield 99.8%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

To a solution of 3-methoxy-4-trifluoromethylsulfonyloxybenzoic acid methyl ester (5 g) in toluene (200 ml) is added tetrakis(triphenylphosphine)palladium (0.9 g) under argon atmosphere, and the mixture is stirred at room temperature for five minutes. To the mixture are added (2-methylphenyl)boric acid (3.2 g), lithium chloride (1.01 g) and a 2M aqueous sodium carbonate solution (11.9 ml), and the mixture is stirred at 100° C. for two hours. To the mixture is added water, and the mixture is filtered through celite to remove the palladium. The filtrate is extracted with diethyl ether, and the ether layer is washed with water, dried, and evaporated. The residue is purified by silica gel column chromatography (solvent; n-hexane→ethyl acetate:n-hexane=1:10) to give 3-methoxy-4-(2-methylphenyl)benzoic acid methyl ester (4.07 g) as oil.

Workup

  1. filtrationthe mixture is filtered through celite
  2. customto remove the palladium
  3. extractionThe filtrate is extracted with diethyl ether
  4. washthe ether layer is washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane→ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-4725c56417c048608b95ebd79129b7e0
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06335327B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes