Methanesulfonyl chloride → 2-(3-Iodophenyl)ethyl methanesulfonate

HRID 15893Notes

Reaction equation

HRID 15893 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[I:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][OH:15])[CH:10]=[CH:11][CH:12]=1.C(N(C(C)C)CC)(C)C>ClCCl.[Cl-].[NH4+]>[CH3:1][S:2]([O:15][CH2:14][CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([I:6])[CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 151698502-(3-Iodophenyl)ethanol

Product 1

HCID 574443702-(3-Iodophenyl)ethyl methanesulfonateYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Methanesulfonyl chloride (1.5 mL, 1.2 eq.) was added dropwise to a stirred solution of 2-(3-iodophenyl)ethanol (3.6 g) in dichloromethane (100 mL) and diisopropylethylamine (3.8 mL, 1.5 equiv.) at 0° C. The solution was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with aqueous ammonium chloride solution and extracted with dichloromethane. The organic layers were combined, washed with aqueous sodium hydrogencarbonate solution, brine, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified using column chromatography (SiO2 cartridge) using DCM-cyclohexane (70:30) to afford the title compound (3.2 g, 45% yield).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with aqueous sodium hydrogencarbonate solution, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified

Sources & evidence

ORD record
ord-9ba5bab4cd0f4a90b639592dfbd117d9
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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