Sodium Iodide → (R)-2-Iodo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol

HRID 1351923Notes

Reaction equation

HRID 1351923 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:6]=1)[OH:4].[Na+].[I-:25]>CC(C)=O>[I:25][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 46938714(R)-2-Bromo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol

Product 1

HCID 53853223(R)-2-Iodo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (R)-2-bromo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (880 mg, 2.2 mmol) and NaI (3.66 g, 24.4 mmol) is refluxed in acetone (35 mL) for one hour. After the mixture is filtered, the filtrate is concentrated, and the residue is separated into ethyl acetate and water. The organic phase is washed with a 25% (w/w) aqueous sodium bisulfite solution, and dried over magnesium sulfate to give the desired (R)-2-iodo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (938 mg, yield: 95%).

Workup

  1. filtrationAfter the mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is separated into ethyl acetate and water
  4. washThe organic phase is washed with a 25% (w/w) aqueous sodium bisulfite solution
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-8174f57b0adb476a927a8728b0c3dc55
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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