Water → HCID 17989159, compound

HRID 1443128Notes

Reaction equation

HRID 1443128 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][CH3:10].C[Si](C)(C)[N-:13][Si](C)(C)C.[K+].O.S(=O)(=O)(O)O.[C:27]1([CH3:33])[CH:32]=CC=C[CH:28]=1>C(OCC)(=O)C>[F:8][C:4]1[C:3]([O:9][CH3:10])=[C:2]([C:27]([CH3:33])([CH3:32])[C:28]#[N:13])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 27368972,6-DifluoroanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 17989159HCID 17989159, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 g (69.39 mol) of 2,6-difluoroanisole is dissolved in 200 ml of toluene and mixed at room temperature with 5.75 g (83.27 mmol) of isobutyric acid nitrile. 166.5 ml of a 0.5 molar solution of potassium hexamethyldisilazide in toluene is added in drops within 35 minutes. In this case, a slight temperature rise to 27.5° C. takes place. After 16 hours of stirring at room temperature, the reaction mixture is mixed with 200 ml of water and 400 ml of ethyl acetate and acidified with 10% sulfuric acid to a pH of 4. The organic phase is separated, and the aqueous phase is shaken once with ethyl acetate (200 ml). The combined organic extracts are shaken with water and brine. After the solvent is dried, filtered and spun off, the residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 7.66 g (57.1%) of the desired compound is isolated.

Workup

  1. customto 27.5° C.
  2. customThe organic phase is separated
  3. stirringthe aqueous phase is shaken once with ethyl acetate (200 ml)
  4. stirringThe combined organic extracts are shaken with water and brine
  5. customAfter the solvent is dried
  6. filtrationfiltered
  7. customthe residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6fdf80331584d089f94169ce8a43d00
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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