1-(Bromomethyl)-4-chlorobenzene → HCID 21867552, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the indole of Step 4 (2.4 g, 6 mmol) in Et2O (50 mL) at −78° C. was added t-BuLi (7 mL, 12 mmol). The reaction mixture was stirred for 10 minutes at −78° C. and p-chlorobenzyl bromide (3.6 g, 18 mmol) was added. The reaction mixture was stirred for 2 hours at r.t. and was quenched with saturated aqueous NH4Cl. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 5% EtOAc in Hexanes to provide 1.9 g of the title compound as a pale yellow oil used as such.

Provenance & Evidence