Sodium Iodide → HCID 57429270, compound

HRID 1817751Notes

Reaction equation

HRID 1817751 reaction equation
[Br:1][C:2]1[CH:3]2O[CH:10]([CH:11]=1)[C:9]1[C:4]2=[CH:5][CH:6]=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=1.[Na+].[I-].C[Si](Cl)(C)C>CC#N>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]([F:15])([F:16])[F:17])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 15533617HCID 15533617, compound

Product 1

HCID 57429270HCID 57429270, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-6-(trifluoromethoxy)-1,4-dihydro-1,4-epoxynaphthalene [ref: Schlosser, M., Castgnetti, E., Eur. J. Org. Chem. 2001, 3991-3997] (1.09 g, 3.55 mmol) and NaI (1.6 g, 10.7 mmol) were dissolved in dry CH3CN (40 ml), followed by addition of TMSCl (1.35 ml, 10.7 mmol). The reaction was stirred for 2.5 h, quenched with 5% Na2SO3, and extracted with ether. The ether solution was washed with 5% Na2SO3, brine, and dried over Na2SO4. The crude product was chromatographed (SiO2, hexanes) to give 2-bromo-6-(trifluoromethoxy)naphthalene as white crystals. NMR (500 MHz, CDCl3) δ: 7.36 (dd, J=2.6, 9.0 Hz, 1H); 7.60 (dd, J=2.0, 8.8 Hz, 1H); 7.63 (br s, 1H); 7.69 (d, J=8.8 Hz, 1H); 7.77 (d, J=9.0 Hz, 1H);8.01 (d, J=2.0 Hz, 1H).

Workup

  1. customquenched with 5% Na2SO3
  2. extractionextracted with ether
  3. washThe ether solution was washed with 5% Na2SO3, brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was chromatographed (SiO2, hexanes)

Sources & evidence

ORD record
ord-476208c8775b4fe7bd3bdaa20e18a882
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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