Sodium Carbonate → HCID 22390458, compound

HRID 1018806Notes

Reaction equation

HRID 1018806 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 X.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-02e63c86002b46f09097c94548858587
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

Loading…