Sodium Carbonate → Methyl (3-(2-methoxyphenyl)phenyl)acetate

HRID 1757065

Reaction equation

HRID 1757065 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.[Cl-].[Na+].C(OCC)(=O)C>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>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 86643102Sodium chloride ethyl acetate

Product 1

HCID 10848669Methyl (3-(2-methoxyphenyl)phenyl)acetateYield 121.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Methyl (3-bromophenyl)acetate (2.06 g, 9.0 mmol), tetrakis(triphenylphosphine)palladium (0)(115 mg), sodium carbonate (2.61 g, 25 mmol in 2 ml water) and toluene (10 ml) were degassed under nitrogen in a 25 ml flask fitted with a reflux condenser. 2-Methoxybenzene boronic acid (1.5 g, 9.87 mmol) in toluene (1 ml) was added and the mixture was heated at reflux overnight, then mixed with 1:1 saturated sodium chloride/ethyl acetate (15 ml). The organic materials were separated, dried (MgSO4), then concentrated under reduced pressure which gave 2.81 g of methyl (3-(2-methoxyphenyl)phenyl)acetate.

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux overnight
  4. customThe organic materials were separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure which

Sources & evidence

ORD record
ord-8d532893c93448bd8ffcb6ccfbc7a72e
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Linked notes

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