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Sodium Carbonate → [1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl ester

HRID 54197
Notes
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Reaction equation

HRID 54197 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.[Cl-].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 27339582-Methoxyphenylboronic acidHCID 86643102Sodium chloride ethyl acetate

Product 1

HCID 5152372[1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 1140TolueneSolvent2×

Procedure

Methyl 3-bromobenzoate (1.99 g, 9.25 mmol), tetrakis(triphenylphosphine) palladium(O) (110 mg), sodium carbonate (2.04 g, 19 mmol in 5 ml water) and toluene (10 ml) were degassed under nitrogen in a 25 ml flask fitted with a reflux condenser. 2-Methoxybenzeneboronic acid (1.46 g, 9.61 mmol) in toluene (1 ml) was added and the mixture was heated at reflux for two days then mixed with 1:1 saturated sodium chloride/ethyl acetate (15 ml). The organic materials were separated, dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient hexane to 8:1 hexane/ethyl acetate) which gave methyl 3-(2-methoxyphenyl)benzoate (1.43 g, 64%), m.p.: 92°-93° C.

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux for two days
  4. customThe organic materials were separated
  5. dry with materialdried (MgSO4)
  6. concentrationthen concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, gradient hexane to 8:1 hexane/ethyl acetate) which

Sources & evidence

ORD record
ord-45bccc0fd90f4902bf29bd9f65b6b1e9
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05622937

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes