Sodium Iodide → HCID 15148994, compound

HRID 1627962Notes

Reaction equation

HRID 1627962 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=[O:3].[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Na+].[I-].CCN(CC)CC.C([O-])(O)=O.[Na+]>CC#N>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([O:3][Si:15]([C:12]([CH3:14])([CH3:13])[CH3:11])([CH3:17])[CH3:16])=[CH2:1])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7466p-BromoacetophenoneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 15148994HCID 15148994, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 250 mL round bottom flask was charged with 4-bromoacetophenone (1.99 g, 10.0 mmol), TBSCl (6.03 g, 40.0 mmol) and NaI (6.00, 40 mmol). The flask was capped with a rubber septum and placed under an atmosphere of Argon. After the addition of 200 mL MeCN, NEt3 (6.13 mL, 44.0 mmol) was introduced and the reaction mixture was stirred for 16 h at rt until TLC monitoring indicated complete conversion. The reaction mixture was poured onto sat. NaHCO3 solution and extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and evaporated to yield a brown slurry. Hexanes was added and the obtained heterogeneous mixture was filtered through a short plug of silica using hexanes to afford the title compound as a colorless oil (3.02 g, 96% yield). Rf=0.49 (1% EtOc/hexanes); 1H NMR (500 MHz, CDCl3) δ 7.47 (d, J=8.5 Hz, 2H), 7.44 (d, J=8.5 Hz, 2H), 4.88 (s, 1H), 4.44 (s, 1H), 1.00 (s, 9H), 0.21 (s, 6H); 13C NMR (125 MHz, CDCl3) δ 155.2, 137.0, 131.4, 127.1, 122.4, 91.6, 26.0, 18.5, −4.4; HR-MS(ESI): calcd. For C14H21ObrSi (M+): 312.0545; found: 312.0542.

Workup

  1. customThe flask was capped with a rubber septum
  2. additionwas introduced
  3. extractionextracted with EtOAc (3×40 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customto yield a brown slurry
  8. filtrationthe obtained heterogeneous mixture was filtered through a short plug of silica

Sources & evidence

ORD record
ord-61cfd2dbea3d4cb792632a2cd4ba02eb
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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