Imidazole → Tridecyl iodide

HRID 1754884Notes

Reaction equation

HRID 1754884 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:39]I>ClCCl>[I:39][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 82071-TridecanolHCID 11776Triphenylphosphine

Product 1

HCID 545617Tridecyl iodideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tridecanol (1.08 g, 5.31 mmol) in dichloromethane (20 mL), triphenyl phosphine (1.53 g, 5.84 mmol) and imidazole (0.39 g, 5.84 mmol) were added and cooled to 0° C. I2 (1.48 g, 5.84 mmol) was added and the reaction mixture was stirred at room temperature for 3 h. After completion of starting materials, the reaction mixture was evaporated and diluted with hexane and passed through a Celite™ pad. The combined organic extracts were evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (100-200 mesh silica gel, eluent hexane) to furnish iodotridecane (1.43 g, 84%) as a low melting solid.

Workup

  1. customAfter completion of starting materials, the reaction mixture was evaporated
  2. additiondiluted with hexane
  3. customThe combined organic extracts were evaporated under reduced pressure
  4. customto obtain the crude product which
  5. customwas purified by column chromatography (100-200 mesh silica gel, eluent hexane)

Sources & evidence

ORD record
ord-7c70f6b3d6984c16a97ff3c3dd1b08f2
Source dataset
uspto-grants-2015_10
Patent number
US09169280B2

Reaction notes

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