Sodium Iodide → HCID 67482669, compound

HRID 1817753Notes

Reaction equation

HRID 1817753 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]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 59030836HCID 59030836, compound

Product 1

HCID 67482669HCID 67482669, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-6-(trifluoromethyl)-1,4dihydro-1,4-epoxynaphthalene (624 mg, 2.14 mmol) and sodium iodide (980 mg, 6.54 mmol) were dissolved in 13 mL of dry acetonitrile and trimethylsilyl chloride (0.823 mL, 6.54 mmol) added. The resultant mixture was stirred at ambient temperature for 3.5 h, poured into hexanes, and the organic layer washed successively with two portions of water and one portion of brine. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and the residue purified by flash column chromatography (SiO2, 5% ethyl acetate/hexanes) to give 2-bromo-6-(trifluoromethyl)naphthalene as a white solid. 1H NMR (500 MHz, CDCl3) δ: 8.15 (s, 1H); 8.11 (s, 1H); 7.89 (d, J=8.7 Hz, 1H); 7.83 (d, J=8.7 Hz, 1H); 7.70 (dd, J=1.6, 8.7 Hz, 1H); 7.69 (dd, J=1.8, 8.7 Hz, 1H).

Workup

  1. washthe organic layer washed successively with two portions of water and one portion of brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash column chromatography (SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d20002c4bf144272a3e5cbbc8476fc1b
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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