Lithium Chloride → HCID 54551655, compound

HRID 343939Notes

Reaction equation

HRID 343939 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5](S(C(F)(F)F)(=O)=O)[CH:4]=1)#[N:2].[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)CCC.[F-].[K+]>O1CCOCC1.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.C(OCC)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 607632TributylphenyltinHCID 540020714-Cyano-2-trifluoromethylsulphonylbenzaldehyde

Product 1

HCID 54551655HCID 54551655, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium [0] (40 mg) was added to a stirred mixture of 4-cyano-2-trifluoromethylsulphonylbenzaldehyde (0.45 g, 1.6 mmol), lithium chloride (0.2 g, 4.8 mmol) and tri-n-butylphenylstannane (0.55 ml, 1.7 mmol) in dried dioxan (10 ml) under nitrogen atmosphere. The resulting suspension was heated under reflux for 24 hours. The dark mixture was cooled, and aqueous potassium fluoride solution (30 ml) and ethyl acetate (30 ml) were added. After vigorous stirring, the black precipitate was filtered and the filtrate layers separated. The ethyl acetate solution was washed with brine (30 ml), dried, filtered and evaporated to a yellow semi-solid (0.72 g). Chromatography on flash silica eluting with chloroform gave 4-cyano-2-phenylbenzaldehyde as a white solid, m.p. 75° C.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe dark mixture was cooled
  4. filtrationAfter vigorous stirring, the black precipitate was filtered
  5. customthe filtrate layers separated
  6. washThe ethyl acetate solution was washed with brine (30 ml)
  7. customdried
  8. filtrationfiltered
  9. customevaporated to a yellow semi-solid (0.72 g)

Sources & evidence

ORD record
ord-30e036357de74a41990149957f2c4694
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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