Imidazole → 1-(2-Iodoethyl)-4-nitrobenzene

HRID 1787705Notes

Reaction equation

HRID 1787705 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH3:11])=[CH:6][CH:5]=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:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5923761-(4-Nitrophenyl)ethan-1-ol

Product 1

HCID 113464461-(2-Iodoethyl)-4-nitrobenzeneYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 g of 4-nitrophenylethanol, 28.1 g of triphenylphosphine and 9.2 g of imidazole are dissolved in 500 ml of THF, mixed in portions with 27.77 g of iodine and stirred for 2 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, 23.22 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-20931d4c8bc648dea128a75c22c23fa2
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

Loading…