Potassium Iodide → Bis(eta-cyclopentadienyl) iron

HRID 433841Notes

Reaction equation

HRID 433841 reaction equation
BrCCCC([C-:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)=O.[CH-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:17].[I-].[K+].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH-:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.[CH-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:17]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 178520530HCID 178520530, compound

Product 1

HCID 7611Bis(eta-cyclopentadienyl) ironYield 15%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(9-azabicyclo[3.3.1] nonan-3a-yl)-N′-(2-methoxy-5-methylphenyl) carbamate (350 mg, 1.15 mmol) in toluene (10 mL) was added 4-bromobutyrylferrocene (385 mg, 1.15 mmol), potassium iodide (166 mg, 1.00 mmol), and triethylamine (500 mg, 4.94 mmol). The reaction mixture was refluxed overnight. Upon completion of reaction (as shown by TLC), the mixture was cooled to room temperature. Silica gel (1 g) was added, and the solvent was evaporated. The resulting solid was layered onto a silica gel column and eluted with 5% methanol in methylene chloride. The desired compound was isolated in 15 % yield (100 mg): mp 94-95° C.; 1H NMR (300 MHz, CDCl3) δ 7.89 (s, 1H), 7.13 (s, 1H), 6.75-6.84 (m, 2H), 5.19-5.21 (m, 1H), 4.80 (s, 2H), 4.56 (s, 2H), 4.21 (s, 5H), 3.92 (s, 3H), 3.65 (s, 2H), 3.16-3.24 (m, 2H), 2.90-2.98 (m, 4H), 2.40-2.52 (m, 3H), 2.31 (s, 3H), 2.00-2.06 (m, 3H), 1.70-1.78 (m, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customUpon completion of reaction (as shown by TLC)
  3. additionSilica gel (1 g) was added
  4. customthe solvent was evaporated
  5. washeluted with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-f75b78b45a1945618773fc546f93acaa
Source dataset
uspto-grants-2003_12
Patent number
US06669925B1

Reaction notes

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