Sodium Carbonate → HCID 22390458, compound

HRID 1071921Notes

Reaction equation

HRID 1071921 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[Cl:16])(=O)=O.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>O.C1(C)C=CC=CC=1.C(O)C.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:16][C:8]1[CH:9]=[C:10]([C:13](=[O:15])[CH3:14])[CH:11]=[CH:12][C:7]=1[C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 22390436HCID 22390436, compound

Product 1

HCID 22390458HCID 22390458, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

19.7 g of 4-acetyl-2-chlorophenyl trifluoromethanesulphonate (compound Va.1), 10 g of 4-fluorobenzeneboronic acid, 2 g of tetrakis(triphenylphosphine)palladium, 17.9 g of sodium carbonate in 84.5 ml of water, 591 ml of toluene, 200 ml of ethanol and 5.51 g of lithium chloride are stirred under an inert atmosphere at 60° C. for 8 hours. The reaction mixture is then stirred for 12 hours at room temperature. The resulting mixture is filtered and the solvents are evaporated from the filtrate under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture; yield=94%.

Workup

  1. filtrationThe resulting mixture is filtered
  2. customthe solvents are evaporated from the filtrate under reduced pressure
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica gel
  5. washeluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-d974aa0b8b1440c2bebb33a163fe49cb
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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