Imidazole → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-iodoethyl)benzonitrile

HRID 474640Notes

Reaction equation

HRID 474640 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:20]I.N1C=CN=C1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:42]=[CH:41][C:40]([CH2:43][CH2:44]O)=[CH:39][C:36]=2[C:37]#[N:38])=[CH:30][C:29]=1[C:46]([F:49])([F:48])[F:47]>C(Cl)Cl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][I:20])=[CH:39][C:36]=2[C:37]#[N:38])=[CH:30][C:29]=1[C:46]([F:49])([F:48])[F:47]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 668256932-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-hydroxyethyl)benzonitrile

Product 1

HCID 677768282-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-iodoethyl)benzonitrileYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Ph3P (1036 mg, 3.95 mmol) and iodine (1003 mg, 3.95 mmol) in DCM (5 mL), which was stirred at room temperature for 10 min, was added imidazole (448 mg, 6.58 mmol). After stirring for another 10 min, 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-(2-hydroxyethyl)benzonitrile (900 mg, 2.63 mmol) was added. The mixture was stirred at room temperature for 1 h, and quenched by water, extracted with DCM. Purification via flash chromatography then afforded the title compound (1.0 g, 2.214 mmol, 84% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. customquenched by water
  3. extractionextracted with DCM
  4. customPurification via flash chromatography

Sources & evidence

ORD record
ord-a5893f2c6356405aa6571f721c37bfce
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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