Trichloroacetonitrile → 1-(4-Bromophenyl)-2-methylpropyl 2,2,2-trichloroethanimidoate

HRID 1180416Notes

Reaction equation

HRID 1180416 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[Cl:15][C:16]([Cl:20])([Cl:19])[C:17]#[N:18].CC(C)=O.CCOC(C)=O>CCOCC.CCOC(C)=O>[Cl:15][C:16]([Cl:20])([Cl:19])[C:17](=[NH:18])[O:14][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=1)[CH:11]([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 21584569Ethylacetate acetoneHCID 217141961-(4-Bromophenyl)-2-methylpropan-1-ol

Product 1

HCID 694708711-(4-Bromophenyl)-2-methylpropyl 2,2,2-trichloroethanimidoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium Hydride (60%, 0.87 mmol) was suspended in Et2O (9 mL) and a solution of 1-(4-bromophenyl)-2-methylpropan-1-ol of step 1 (8.7 mmol, 2.0 g) in Et2O (6 mL) was added. The mixture was stirred at r.t. for 0.25 h. The mixture was cooled to 0° C. Trichloroacetonitrile (11 mmol) was added. The mixture was allowed to warmed to r.t. over 1 h. The mixture was diluted with EtOAc and washed with NaHCO3. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography (10% Acetone/EtOAc) gave the title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C
  2. temperatureto warmed to r.t. over 1 h
  3. washwashed with NaHCO3
  4. extractionThe organic extract
  5. dry with materialwas dried (anhyd. MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil

Sources & evidence

ORD record
ord-142af91266e744b4b609d90cbd29a67b
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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