Hydrochloric Acid → HCID 17989091, compound

HRID 1443281Notes

Reaction equation

HRID 1443281 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4](F)[C:3]=1[O:10][CH3:11].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:22](#[N:26])[CH:23]([CH3:25])[CH3:24].Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([C:23]([CH3:25])([CH3:24])[C:22]#[N:26])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6559IsobutyronitrileHCID 27741352,6-Difluoro-3-methylanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 17989091HCID 17989091, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

14.48 g (91.56 mmol) of 2,6-difluoro-3-methylanisole is dissolved in 800 ml of toluene. After 272.2 ml (137.35 mmol) of a 0.5 molar solution of potassium hexamethyl disilazide in toluene is added, 25.31 g (366.26 mmol) of isobutyronitrile is added in drops. The batch is stirred for 10 days at room temperature and then added to a 1 M HCl solution. After being extracted three times with methyl tert-butyl ether, the combined organic extracts are washed with saturated NaCl solution and dried. After spinning-in and chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 10.32 g (49.5%) of the desired compound is obtained.

Workup

  1. extractionAfter being extracted three times with methyl tert-butyl ether
  2. washthe combined organic extracts are washed with saturated NaCl solution
  3. customdried

Sources & evidence

ORD record
ord-be6e7a18a0434fddb6fcd99ccec96808
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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