N,N,N',N'-Tetramethylethylenediamine → 1,1'-(Pentane-2,4-diyl)dibenzene
Reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH2:12][CH2:13]N(C)C)C.Cl[CH:18]([CH2:20][CH:21](Cl)[CH3:22])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]1([CH:18]([CH2:20][CH:21]([C:13]2[CH:12]=[CH:3][CH:2]=[CH:1][CH:6]=2)[CH3:22])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
A mixture of phenyl magnesium bromide (1.25 mL of 0.96 M THF solution, 1.2 mmol) and TMEDA (181.1 μL, 1.2 mmol) was added to a solution of 2,4-dichloropentane (70.5 mg, 0.5 mmol) and FeCl3 (0.5 mL of 0.1 M THF solution, 0.05 mmol) in THF (0.5 mL) at 50° C. over an hour through a syringe pump. The resulting mixture was stirred at the temperature for 20 minutes and saturated ammonium chloride aqueous solution was added thereto to terminate the reaction, followed by diluting with 3 mL of ethyl acetate. The dilution was filtered through a packed silica gel (eluent: ethyl acetate) followed by concentration under reduced pressure. 1H NMR analysis indicates that the desired product was obtained in almost quantitative yield. Purification by recycling GPC gave the pure compound in a yield of 71%.
Workup
- customto terminate
- customthe reaction
- filtrationThe dilution was filtered through a packed silica gel (eluent: ethyl acetate)
- concentrationfollowed by concentration under reduced pressure
- customwas obtained in almost quantitative yield
- customPurification
- customgave the pure compound in a yield of 71%
Sources & evidence
- ORD record
- ord-ddfcef9722f9420fb90054b2f89f33f2
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781599B2
Reaction notes
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