Sulfuric Acid → HCID 17989209, compound

HRID 420634Notes

Reaction equation

HRID 420634 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

16.7.8 g (93.97 mmol) of 3-chloro-2,6-difluoroanisole 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. The temperature in this case 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 with 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 with saturated NaCl solution
  3. customdried

Sources & evidence

ORD record
ord-6c47fad82ae343f2b9182c2f52872fcd
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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