Allyl bromide → HCID 10890478, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence