Methanesulfonyl chloride → 2-Iodo-4-nitrobenzyl Methanesulfonate

HRID 541793

Reaction equation

HRID 541793 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12].C(N(CC)C(C)C)(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[I:1])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 279258(2-Iodo-4-nitrophenyl)methanol

Product 1

HCID 579616812-Iodo-4-nitrobenzyl MethanesulfonateYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-iodo-4-nitrophenyl)methanol (6.01 g, 21.5 mmol) in methylene chloride (50 mL) was added N,N-diisopropylethylamine (7.50 mL, 43.1 mmol) and methanesulfonyl chloride (1.83 mL, 23.7 mmol) at 0° C. The reaction solution was stirred at same temperature for 2 hours. The reaction was quenched with water, and aqueous layer was extracted with DCM once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated The crude product was purified by flash column chromatography to give the desired product (6.15 g, 80%). LCMS calculated for C8H91NO5S (M+H)+: m/z=358.0.

Workup

  1. customThe reaction was quenched with water, and aqueous layer
  2. extractionwas extracted with DCM once
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated The crude product
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f70d53f84da043fe9c4d78d92e66e455
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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