Sulfuric Acid → HCID 17989209, compound

HRID 1443299Notes

Reaction equation

HRID 1443299 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([O:9][CH3:10])[C:5](F)=[CH:6][CH:7]=1.[C:12](#[N:16])[CH:13]([CH3:15])[CH3:14].C[Si](C)(C)[N-][Si](C)(C)C.[K+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([CH3:15])([CH3:14])[C:12]#[N:16])=[C:4]([O:9][CH3:10])[C:3]=1[F:11]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6559IsobutyronitrileHCID 27735083-Chloro-2,6-difluoroanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 17989209HCID 17989209, compoundYield 34.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
28 °C

Procedure

16.78 g (93.97 mmol) of 3-chloro-2,6-difluoro-anisole is dissolved in 800 ml of toluene. After 25.97 g (375.88 mmol) of isobutyronitrile is added, 283.97 ml (140.95 mmol) of a 0.5 molar solution of potassium hexamethyl disilazide in toluene is added in drops. In this case, the temperature increases to 28° C. The batch is stirred for seven days at 60° C. After mixing with water and ethyl acetate, the reaction mixture is brought to a pH of 4 with 1 M sulfuric acid. After being extracted twice with ethyl acetate, the combined organic extracts are washed with water and saturated NaCl solution and dried. After spinning-in and chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 7.46 g (21.4%) of the desired compound is obtained.

Workup

  1. extractionAfter being extracted twice with ethyl acetate
  2. washthe combined organic extracts are washed with water and saturated NaCl solution
  3. customdried

Sources & evidence

ORD record
ord-a48319c57c6540e8afa26940f5468bde
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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