Hydrochloric Acid → HCID 23533987, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-Iodobenzoate (10.0 g, 36.2 mmol) in DMF (30 mL) was added 3-fluorophenylacetylene (5.22 g, 43.4 mmol), Pd(Ph3P)4 (1.04 g, 0.91 mmol), CuI (346 mg, 1.82 mmol) and diethylamine (6 mL). The reaction vessel was sealed and heated at 60° C. for 1 h in a microwave reactor. The reaction was cooled to room temperature, diluted with EtOAc:hexanes (2:1, 250 mL) and washed with water (2×200 mL) and brine (200 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was dissolved in THF (130 mL) added MeOH (28 mL) and a solution of LiOH (3.04 g, 72.4 mmol) in water (28 mL). The reaction was stirred at room temperature and for 4 h. The reaction was acidified with 1 N HCl (100 mL) and 4-((3-fluorophenyl)ethynyl)benzoic acid was isolated (6.89 g, 79%) as a light tan solid; 1H-nmr (400 MHz, d6-DMSO) δ 7.97 (d, J=8.5 Hz, 2H), 7.68 (d, J=8.5 Hz, 1H), 7.55-7.42 (m, 3H), 7.21 (td, J=8.0, 2.0 Hz, 1H); LC (290 nM) 5.27 min (>98%); MS (ESI) m/z=240.7.

Provenance & Evidence