Sodium Carbonate → HCID 17965980, compound

HRID 1348887Notes

Reaction equation

HRID 1348887 reaction equation
Cl[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl.C(O)C>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 83343Methyl 2-chloro-4-nitrobenzoateHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 17965980HCID 17965980, compoundYield 99.4%

Reagents, catalysts & solvents 4

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)CatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-chloro-4-nitrobenzoate (0.432 g, 2.0 mmol), 3-chlorophenylboronic acid (0.375 g, 2.4 mmol), trans-dichlorobis(tricyclohexylphosphine)-palladium (II) (0.074 g, 0.1 mmol), and sodium carbonate (0.64 g, 6.0 mmol) in a mixture of toluene (10 mL), dioxane (10 mL), and ethanol (2 mL) was heated to reflux for 12 hours, cooled to room temperature, diluted with ethyl acetate (10 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes to provide 0.58 g (99%) of the desired product. MS (DCI/NH3) m/z 309 (M+NH4)+; 1H NMR (CDCl3) δ 8.27-8.22 (m, 2H), 8.00 (dd, 1H), 7.41-7.34 (m, 3H), 7.23-7.18 (m, 1H), 3.72 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-eba5564ff91749a7a04dedf78fcc2c06
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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