Sodium Carbonate → HCID 67126522, compound

HRID 1848814Notes

Reaction equation

HRID 1848814 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4](OS(C(F)(F)F)(=O)=O)[CH2:3]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOCC.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>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:4]2[CH2:3][C:2]([CH3:20])([CH3:1])[O:7][CH2:6][C:5]=2[C:8]([O:10][CH3:11])=[O:9])=[CH:24][CH:23]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 87279388HCID 87279388, compound

Product 1

HCID 67126522HCID 67126522, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of EXAMPLE 38B (2.88 g), 4-chlorophenylboronic acid (1.88 g) and tetrakis(triphenylphosphine)palladium(0) (0.578 g) in toluene (40 mL) and ethanol (10 mL) was added 2N aqueous Na2CO3 (10 mL). The mixture was stirred at reflux overnight. The mixture was diluted with ether (300 mL) and washed with water, brine and dried over Na2SO4. After filtration and evaporation of solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give the product.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and evaporation of solvent
  5. washeluted with 3% ethyl acetate in hexane
  6. customto give the product

Sources & evidence

ORD record
ord-a744f17ff41b4279a5710fcd5c55e000
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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