Allyl bromide → HCID 59324097, compound

Participants

Reaction Conditions

Reaction Steps

A solution of t-butyllithium in pentane (1.7M, 5.7 ml, 9.84 mmol) was added in portions to a solution of 2,4,6-trimethylphenylbromide (0.744 ml, 980 mg, 4.93 mmol) in 8 ml THF at ca −78° C. A white precipitate was formed. After 10 minutes at low temperature a solution of 2-(2,3-dimethyl-phenoxymethyl)-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester (1 g, 3.28 mmol) in 6 ml THF was added in portions to give an orange solution. This was warmed to −20° C. and cooled again to ca −70° C. whereupon much of the solid went into solution. Allyl bromide (0.332 ml, 475 mg, 3.93 mmol) was added and the reaction mixture stirred for 30 min at this temperature before a small amount of acetic acid was added. The mixture was warmed and shaken between EtOAc and water. The organic phase was dried with Na2SO4 and evaporated to give 1.3 g of crude product, which was chromatographed on silica to yield 2-[1-(2,3-dimethyl-phenoxy)-but-3-enyl]-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester. 1H-NMR (CDCl3) (selection) 5.10 (d, allyl), 5.18 (d, allyl), 5.66 (t, OCH), 5.98 (m, allyl)

Provenance & Evidence