Potassium Hydroxide → 3-Bromostyrene

To a solution of 1-bromo-3trimethylsilylethynylbenzene (20.5 g, 81.0 mmol) in degassed methanol (500 ml) was added potassium hydroxide (31 mg, 0.55 mmol) in water (1 ml). The solution was stirred at room temperature until G.C. analysis indicated the reaction was complete (5.0 h). The reaction mixture was diluted with an equal volume of water, and extracted with n-pentane (5×500 ml). The combined organic layers were dried (MgSO4) and the solvent removed under reduced pressure to yield a yellow liquid. The liquid was distilled via bulb-to-bulb vacuum distillation to yield the product (1c) (13.0 g, 90%) as a clear liquid: bp 40° C.C/1 torr; 1H NMR (200 MHz, CDCl3) c3.35(s), 7.23(t), 7.40(m), 7.65(t).

1. custom(5.0 h)
2. extractionextracted with n-pentane (5×500 ml)
3. dry with materialThe combined organic layers were dried (MgSO4)
4. customthe solvent removed under reduced pressure
5. customto yield a yellow liquid
6. distillationThe liquid was distilled via bulb-to-bulb vacuum distillation

ORD record

ord-1d5b374d862c4e908ee94bca488ea912

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05453169