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

HRID 1466098Notes

Reaction equation

HRID 1466098 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37]O)=[CH:32][CH:31]=1)([O-:29])=[O:28]>C(Cl)Cl>[I:25][CH2:37][CH2:36][C:33]1[CH:34]=[CH:35][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 74944-Nitrophenethyl alcoholHCID 11776Triphenylphosphine

Product 1

HCID 113464461-(2-Iodoethyl)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of triphenylphosphine (1.9 g, 7.2 mmol) and imidazole (489 mg, 7.18 mmol) in DCM (20 ml) was added iodine (1822 mg, 7.18 mmol) to form a solution. Small portions of 2-(4-nitrophenyl)ethanol (1.0 g, 6.0 mmol) was added to the suspension. TLC showed conversion to the desired product quickly. Hexane was added to the reaction to precipitate side products which were filtered off. The filtrate was concentrated in vacuo to obtain crude 1-(2-iodoethyl)-4-nitrobenzene, which was purified by silica gel flash chromatography using Hexane and EtOAc system. 1H-NMR (500 MHz, CD3Cl) δ 8.22 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 3.41 (t, J=7.0 Hz, 2H), 3.32 (t, J=7.0 Hz, 2H).

Workup

  1. customto form a solution

Sources & evidence

ORD record
ord-0999f1da8b7048c9a78143703ac5c0cd
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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