2-Bromopyridine → 2-(2,4,6-trimethylphenyl)pyridine

HRID 1510185Notes

Reaction equation

HRID 1510185 reaction equation
C1COCC1.[C:6]1([CH3:16])[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[Mg]Br.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C>CCCCCC.CCOC(C)=O>[CH3:16][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDEHCID 178425415HCID 178425415, compound

Product 1

HCID 113446132-(2,4,6-trimethylphenyl)pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using a THF solution of mesitylmagnesium bromide (0.974 mL, 0.77 M, 0.75 mmol), 2-bromopyridine (158.0 mg, 1.0 mmol), FeF3.3H2O (5.01 mg, 0.03 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (38.4 mg, 0.09 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 90° C. for 24 hours in the same manner as in Example 2. After performing silica gel column chromatography (EtOAc=10 and 20% in hexane), the above compound was obtained as a yellow liquid (0.150 g, yield=76%, purity=>99% (GC analysis)).

Workup

  1. customthe above compound was obtained as a yellow liquid (0.150 g, yield=76%, purity=>99% (GC analysis))

Sources & evidence

ORD record
ord-2b1b37d6376d49fa977ab0db0cbd88d7
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

Loading…