Triphenylphosphine → HCID 58902319, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenylphosphine (1.2 g, 0.0048 mol) and 3-tert-butyl-5-(hydroxymethyl)benzoic acid (1.0 g, 0.0048 mol) in acetone (20 mL) at −18° C. was added N-bromosuccinimide (0.85 g, 0.0048 mol) portionwise over 2 minutes. After 5 minutes, pyrrolidine (0.96 mL, 0.012 mol) was added. The reaction mixture was heated at 80° C. overnight. EtOAc and water were added to the reaction mixture. The phases were separated and the organic solution was washed with 1M NaOH, 1M HCl, and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give 3-tert-butyl-5-(pyrrolidin-1-ylmethyl)benzoic acid (6%). LCMS ES+ 262, ES− 260.

Provenance & Evidence