Sodium Iodide → tert-Butyl-(2-fluoro-4-iodo-benzyloxy)-dimethyl-silane

HRID 564067Notes

Reaction equation

HRID 564067 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[C:4]([F:17])[CH:3]=1.[I-:18].[Na+].CN(C)CCN>O1CCOCC1.N>[C:11]([Si:8]([O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([I:18])=[CH:3][C:4]=1[F:17])([CH3:10])[CH3:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 66053N,N-DimethylethylenediamineHCID 57685175((4-Bromo-2-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

Product 1

HCID 67007573tert-Butyl-(2-fluoro-4-iodo-benzyloxy)-dimethyl-silane

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 7.70 g (24.1 mmol) (4-bromo-2-fluoro-benzyloxy)-tert-butyl-dimethyl-silane (preparation 16a) in 8 mL 1,4-dioxane is added 937 mg (4.82 mmol) Cu(I)-iodide. The reaction mixture is flushed with argon and 7.23 g (48.2 mmol) sodium iodide and 1.03 mL (9.65 mmol) N,N-dimethylethylen-diamine are added. The mixture is stirred at 120° C. for 7 h in a sealed tube. The reaction mixture is diluted at RT with 5% aqueous NH3-solution and the aqueous phase is extracted with EtOAc. The combined organic phase is washed a few times with water, dried over MgSO4, filtered and the solvent is evaporated.

Workup

  1. additionare added
  2. extractionthe aqueous phase is extracted with EtOAc
  3. washThe combined organic phase is washed a few times with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-a2ddbe30031644f98d7896cc62d2e042
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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