Imidazole → Methanesulfonic acid 2-iodomethyl-5-methylphenyl ester

HRID 889238Notes

Reaction equation

HRID 889238 reaction equation
N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:25]I.O[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1[O:36][S:37]([CH3:40])(=[O:39])=[O:38]>C(Cl)Cl>[I:25][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1[O:36][S:37]([CH3:40])(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 86638980Methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester

Product 1

HCID 86638982Methanesulfonic acid 2-iodomethyl-5-methylphenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidazole (4.5 g, 66.6 mmol) and PPh3 (17.4 g, 66.6 mmol) in DCM (180 mL) is slowly added over a period of 10 min of I2 (16.9 g, 66.6 mmol) and it is stirred at RT for 30 min. Then a solution of methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester (12.0 g, 55.5 mmol) in DCM (40 mL) is added drop wise and it is stirred at RT for 1 h. The reaction mixture is concentrated to about 70 mL. It is then filtered and washed with DCM. The filtrate is concentrated and purified to give the title compound as a solid.

Workup

  1. stirringit is stirred at RT for 1 h
  2. concentrationThe reaction mixture is concentrated to about 70 mL
  3. filtrationIt is then filtered
  4. washwashed with DCM
  5. concentrationThe filtrate is concentrated
  6. custompurified

Sources & evidence

ORD record
ord-078e7baf27854c9d8a5d867aaab1c13c
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

Loading…