Sodium Carbonate → (4-Chloro-2-methylphenyl)(3-methoxyphenyl)methanone

HRID 854879Notes

Reaction equation

HRID 854879 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([CH3:22])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.Cl[Pd]Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:7])=[C:15]([CH3:22])[CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 74374m-Anisoyl chlorideHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

Product 1

HCID 69518452(4-Chloro-2-methylphenyl)(3-methoxyphenyl)methanone

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a chilled stirred solution of 3-methoxybenzoyl chloride (5.0 g, 29.3 mmole) in acetone/water (3:1) was added 4-chloro-2-methylphenylboronic acid (5.0 g, 29.3 mmole) followed by PdCl2 (0.259 g, 5 mole %) and sodium carbonate (23.87 mL, 47 mmole). The solution was allowed to stir at room temperature overnight. The reaction workup and purification was conducted according to Example 9a, Step 1 producing the title compound (5.8 g, 76%). This ester was of suitable purity to use without further purification: ESLRMS m/z 261.1 (M+H).

Workup

  1. customThe reaction workup and purification
  2. customto use without further purification

Sources & evidence

ORD record
ord-8cdd4c0e871242d096ac7dc819170619
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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