Acetone → HCID 69517431, compound

HRID 854887Notes

Reaction equation

HRID 854887 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](Cl)=[O:12])[C:6]=1[CH3:14])(=[O:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC(C)=O>Cl[Pd]Cl.O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:12])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:6]=1[CH3:14])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 7010345(3-(Chlorocarbonyl)-2-methylphenyl)acetate

Product 1

HCID 69517431HCID 69517431, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-(chlorocarbonyl)-2-methylphenyl acetate (10.0 g, 47.0 mmole), PdCl2 (83.4 mg, 0.470 mmole), Na2CO3 (8.13 g, 76.7 mmole) and phenyl boronic acid (6.02 g, 49.4 mmole) in a 3:1 acetone:H2O mixture (300 mL) was stirred at room temperature for 5 days. The acetone was removed in vacuo and the aqueous mixture was extracted with EtOAc (2×200 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give 7.68 g (64% yield) of the product as a white crystalline solid: E1HRMS m/z 254.0939 (M+, C16H14O3, Calc'd 254.0943).

Workup

  1. customThe acetone was removed in vacuo
  2. extractionthe aqueous mixture was extracted with EtOAc (2×200 mL)
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fa86d5b52204f8aaedffa2607d333a1
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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