APPLICATION
TCI Practical Example: Bromination Reaction Using N-Bromosuccinimide
Used Chemicals
2-Methylbenzo[b]thiophene [M1429]
N-Bromosuccinimide (= NBS) [B0656]
Acetonitrile
Procedure
A solution of 2-methylbenzo[b]thiophene (500 mg, 3.4 mmol) in acetonitrile (5 mL) was stirred under nitrogen at 0 ËšC. Then NBS (630 mg, 3.5 mmol) was added the solution. The ice bath was removed and the mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was purified by silica gel column chromatography (hexane, Rf = 0.65) to give 3-bromo-2-methylbenzo[b]thiophene as a white solid (759 mg, 99% yield).
Experimenter’s Comments
The reaction mixture was monitored by TLC (hexane, Rf = 0.65).
Analytical Data
3-bromo-2-methylbenzo[b]thiophene
1H NMR (270 MHz, CDCl3); δ 7.70-7.75 (m, 2H), 7.30-7.44 (m, 2H), 2.56 (s, 3H).
Lead Reference
Reactive ligand influence on initiation in phenylene catalyst-transfer polymerization
A. O. Hall, S. R. Lee, A. N. Bootsma, J. W. G. Bloom, S. E. Wheeler, A. J. McNeil, Polym. Chem. 2017, 55, 1530.
Application
A Method for the Synthesis of Acyclic Haloamines with Ring Opening of Cyclic Amines
Experimental procedure:
To a vial, Piv-protected amine (1 eq.), AgNO3 (4 eq.), (NH4)2S2O8 (4 eq.), and NCS or NBS (4 eq.) is added and dissolved in 1:9 acetone:water (0.2 M). The resulting mixture is stirred at room temperature. After 30 minutes, the reaction mixture is partitioned between EtOAc and H2O and separated. The aqueous layer is extracted with EtOAc in triplicate and the combined organic layers concentrated in vacuo. The crude mixture is then purified over silica column eluting with an EtOAc:Hex. Mixture to afford the desired haloamine product.
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