4-Bromotoluene → 3-(4-Methylphenyl)thiophene
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].Br[C:11]1[CH:15]=[CH:14][S:13][CH:12]=1>C1COCC1.C(OCC)C.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl>[S:13]1[CH:14]=[CH:15][C:11]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:12]1Participants
Procedure
A solution of 4-bromotoluene (0.9 ml, 7.3 mmol) in THF (3 ml) is added to dried magnesium turnings (0.815 g, 33.5 atoms) under nitrogen atmosphere. After the exothermic reaction initiates, a solution of 4-bromotoluene (3.16 ml, 25.7 mmol) in THF (3 ml) is dropped to the reaction mixture. The stirring is continued for 10 min. The mixture is dropped to a suspension of 3-bromothiophene (2.8 ml, 29.9 mmol) and [1,2-bis(diphenylphosphino)-ethane]nickel(II) chloride (0.72 g, 1.4 mmol) in diethyl ether (50 ml), which has been stirred for 10 min. The reaction mixture is cooled and quenched with 1N hydrochloric acid and extracted with ether. The organic layer is washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate and concentrated in vacuo. The residue is recrystallized from ethanol to give 4-(3-thienyl)toluene.
Workup
- customAfter the exothermic reaction initiates
- temperatureThe reaction mixture is cooled
- customquenched with 1N hydrochloric acid
- extractionextracted with ether
- washThe organic layer is washed with saturated sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue is recrystallized from ethanol
Sources & evidence
- ORD record
- ord-42ddaed19105494faedb239c3bc9a256
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780498
Reaction notes
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