N-Iodosuccinimide → HCID 67257479, compound

HRID 2371044Notes

Reaction equation

HRID 2371044 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.C1C(=O)N([I:35])C(=O)C1>C1COCC1>[Br:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][O:9][Si:10]([CH:11]([CH3:13])[CH3:12])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])=[CH:4][C:3]=1[I:35]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 2724682Lithium diisopropylamideHCID 67256993HCID 67256993, compound

Product 1

HCID 67257479HCID 67257479, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2-(5-bromothiophen-2-yl)ethoxy)triisopropylsilane (7.24 g, 20 mmol) in dry THF (80 mL) at −5° C. was added LDA (20 mL in THF, 30 mmol) dropwise. After stirred for 1 h, NIS (6.75 g, 30 mmol) in dry THF (20 mL) was added dropwise and the resulting mixture was stirred for another 2 h. The reaction was quenched with water (30 mL) and the resulting mixture was extracted with EtOAc (3×150 mL), washed with brine, dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (5.9 g, 61%).

Workup

  1. stirringthe resulting mixture was stirred for another 2 h
  2. customThe reaction was quenched with water (30 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (3×150 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5e54e60bf8f346a7b1c147299db03d94
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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