1,10-Phenanthroline → 1-Butoxy-2-methylbenzene

HRID 1883403Notes

Reaction equation

HRID 1883403 reaction equation
N1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2N=CC=[CH:9]3)C=CC=1.[C:15]([O-:18])([O-])=O.[Cs+].[Cs+].I[C:22]1[CH:27]=CC=C[C:23]=1C>[Cu]I.C(O)CCC>[CH2:15]([O:18][C:13]1[CH:14]=[CH:5][CH:6]=[CH:7][C:8]=1[CH3:9])[CH2:23][CH2:22][CH3:27]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 51282-IodotolueneHCID 10796Cesium carbonate

Product 1

HCID 50451121-Butoxy-2-methylbenzeneYield 484%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 1,10-phenanthroline (36 mg, 0.20 mmol, 20 mol %), Cs2CO3 (456 mg, 1.4 mmol), 2-iodotoluene (127 μL, 1.0 mmol) and n-butanol (1.0 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 23 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane) provided 159 mg (97% yield) of the title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customPurification of the residue by flash chromatography on silica gel (2×20 cm; hexane)

Sources & evidence

ORD record
ord-52ef12128e504cdba7d072e45bcc8491
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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