2-(Trifluoromethyl)benzoyl chloride → HCID 59314376, compound

Participants

Reaction Steps

A 30 mL vial is charged with 2-aminoindan-2-carboxylic acid (450 mg, 2.19 mmol) and dry DCM (5 mL). A stirring bar is added and stirring is initiated. DIPEA (0.61 mL, 3.51 mmol) is added. 2-(trifluoromethyl)-benzoyl chloride (388 μL, 2.63 mmol) and DMAP (3 mg, cat.) are added. The reaction is capped. After 38 days, tlc analysis (silica, 10% iPrOH/DCM) indicates that the starting is completely consumed. The contents of the reaction flask are transferred to a reparatory funnel and diluted with EtOAc (60 mL). The organic phase is washed with dilute aqueous HCl (2×25 mL), saturated aqueous NaHCO3 (2×25 mL), and brine (25 mL), dried over MgSO4, filtered and evaporated by pumping to constant weight yields 0.84 g of light orange solid. This is diluted with DCM and applied to a silica column ((24 g) on an ISCO Companion. 14 mL fractions of UV positive eluent are collected. Fraction 4-10 are combined and evaporated by pumping to constant weight to give light yellow solid (0.76 g, 92%).

Provenance & Evidence