Trichloroacetonitrile → 2-(4-(Trifluoromethyl)phenyl)propan-2-yl 2,2,2-trichloroacetimidate

HRID 1482393Notes

Reaction equation

HRID 1482393 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:25][C:26]([Cl:30])([Cl:29])[C:27]#[N:28]>C1COCC1>[Cl:25][C:26]([Cl:30])([Cl:29])[C:27](=[NH:28])[O:12][C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:8][CH:7]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27776172-(4-(Trifluoromethyl)phenyl)-2-propanol

Product 1

HCID 896686702-(4-(Trifluoromethyl)phenyl)propan-2-yl 2,2,2-trichloroacetimidateYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2-[4-(Trifluoromethyl)phenyl]propan-2-ol (Compound SP824) (27.0 g, 132 mmol) was azeotropically distilled with THF (54 ml) three times. This was dissolved in dehydrated THF (270 ml) under a nitrogen atmosphere, a solution of sodium bis(trimethylsilyl)amide in dehydrated THF (1.9 M, 13.9 ml, 26.4 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Trichloroacetonitrile (13.3 ml, 132 mmol) was added thereto at 0° C., followed by stirring for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by amino silica gel column chromatography (hexane) to afford 2-(4-(trifluoromethyl)phenyl)propan-2-yl 2,2,2-trichloroacetimidate (Compound SP853) (86%, 39.7g).

Workup

  1. customat 0° C.
  2. stirringby stirring for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by amino silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-4b377d9d9f6f4c8e96a5a0a15e991bfd
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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