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

HRID 964622Notes

Reaction equation

HRID 964622 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 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (R)-2-bromo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol (12.4 g, 31 mmol) and NaI (52 g, 346 mmol) were refluxed in acetone (190 mL) for 1.75 hours. After filtration, the filtrate was concentrated to a pasty red-brown solid which was partitioned between CH2Cl2 (150 mL) and H2O (190 mL). The organic phase was washed with 150 mL ~23.5% w/w aq. sodium bisulfite and with H2O (150 mL), dried over Na2SO4 and concentrated to give the title compound (12.72 g, 91%).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated to a pasty red-brown solid which
  3. customwas partitioned between CH2Cl2 (150 mL) and H2O (190 mL)
  4. washThe organic phase was washed with 150 mL ~23.5% w/w aq. sodium bisulfite and with H2O (150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2a04acb35e3746a99296e3a69b88efcf
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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