Methyl iodide → 3-Bromo-2-methyl-1-benzothiophene
Reaction equation
[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[CH:11](NC(C)C)(C)C.[Li].C1CCCCC1.CI.[NH4+].[Cl-]>>[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][C:6]=1[CH3:11]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
1.06 g of 3-Bromo-benzo[b]thiophene (5.0 mmol) is dissolved in 10 ml of dry tetrahedrofuran and cooled to −78° C. and 3.67 ml of lithium diisopropylamine 1.5M in cyclohexane (5.5 mmol) is added slowly and stirred at −78° C. for 15 min. 0.35 ml of Methyl iodide (5.6 mmol) is added and the reaction mixture is stirred at room temperature for 1 h, sat. NH4Cl is added, and the mixture is extracted with CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=10:1) to give the title compound. 835 mg (74%). 1H-NMR (CDCl3): 7.76 (t, 2H, J=7.7 Hz), 7.46 (t, 1H, J=7.7 Hz), 7.37 (t, 1H, J=7.7 Hz), 2.60 (s, 3H)
Workup
- stirringthe reaction mixture is stirred at room temperature for 1 h
- extractionthe mixture is extracted with CH2Cl2
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-c2822ee6fd1a4030ba0a2bdd663f0cd9
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557103B2
Reaction notes
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