Imidazole → HCID 53237888, compound

HRID 1787704Notes

Reaction equation

HRID 1787704 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10](O)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:37]I.[Cl-].[NH4+]>C1COCC1>[I:37][CH2:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 223135alpha-Methyl-3-nitrobenzenemethanol

Product 1

HCID 53237888HCID 53237888, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g of 3-nitrophenylethanol, 9.4 g of triphenylphosphine and 3.1 g of imidazole are dissolved in 250 ml of THF, mixed in portions with 9.1 g of iodine and stirred for 15 hours at room temperature. The reaction mixture is mixed with ammonium chloride solution and extracted with dichloromethane. The organic phase is washed in succession with sodium thiosulfate solution and water and dried on sodium sulfate. After purification by chromatography on silica gel, 7.51 g of the title compound is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed in succession with sodium thiosulfate solution and water
  3. customdried on sodium sulfate
  4. customAfter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-62e1a56f9c2d4da692d9cff1587c1dbf
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

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