Hexane → 3-Chloro-4-trimethylsilyl-bromobenzene

3-chloro-4-iodobromobenzene (3.1 g) was dissolved in diethyl ether (100 ml). To the solution was then added dropwise a hexane solution of n-butyl lithium (1.59 M, 6.1 ml) at −78° C. The mixture was then stirred at the same temperature for 30 minutes. To the mixture was then added dropwise trimethylsilyl trifluoromethane sulfonate (3.77 ml; 17.4 mmol). The mixture was then stirred for 1 hour. After the quenching of the reaction by gradually adding water over an ice bath, the product was then extracted with ether. The resulting organic phase was then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The crude product thus obtained was then purified twice through silica gel column chromatography (silica gel produced by Merck Ltd., Japan; hexane) to obtain 3-chloro-4-trimethylsilyl-bromobenzene (2.3 g) (yield: 90%).

1. stirringThe mixture was then stirred for 1 hour
2. customAfter the quenching of the reaction by gradually adding water over an ice bath
3. extractionthe product was then extracted with ether
4. dry with materialThe resulting organic phase was then dried over magnesium sulfate
5. distillationThe solvent was then distilled off under reduced pressure
6. customThe crude product thus obtained
7. customwas then purified twice through silica gel column chromatography (silica gel produced by Merck Ltd., Japan; hexane)

ORD record

ord-1c5d2811924e44f1a7679795d4c25ee0

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189790B2