Allyl bromide → HCID 10890478, compound

Temperature

0 °C

A solution of 4-bromophenylacetic acid (12.0 g) of Formula XIII-A in 450 ml of anhydrous THF is cooled to 0° C. via an ice bath. The solution is treated with lithium bis(trimethylsilyl)amide (LiHMDS, 1.0M in THF, 112 ml) which initially results in a light yellow slurry which becomes an orange homogeneous solution. The solution is stirred at 0° C. for 2 hrs followed by warming to room temperature. The solution is recooled to 0° C. and is treated dropwise with allyl bromide (5.0 ml). The mixture is left to stir overnight with gradual warming to room temperature. After 18 hrs the mixture is cooled to 0° C. and quenched with 250 ml of 10% aqueous HCl. The mixture is poured into a separatory funnel and extracted with EtOAc (2×300 ml). The combined organic extracts are dried over anhydrous Na2SO4, filtered and concentrated to give a viscous oil. This material is distilled (0.5 mm Hg, collected 158°-161° C.) to give 10.1 g of the title product.

1. custominitially results in a light yellow slurry which
2. temperatureby warming to room temperature
3. customis recooled to 0° C.
4. waitThe mixture is left
5. stirringto stir overnight
6. temperaturewith gradual warming to room temperature
7. temperatureAfter 18 hrs the mixture is cooled to 0° C.
8. customquenched with 250 ml of 10% aqueous HCl
9. additionThe mixture is poured into a separatory funnel
10. extractionextracted with EtOAc (2×300 ml)
11. dry with materialThe combined organic extracts are dried over anhydrous Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto give a viscous oil
15. distillationThis material is distilled
16. custom(0.5 mm Hg, collected 158°-161° C.)

ORD record

ord-d80a929c07dd4465b3587256a2b94476

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05708169