P-Chloroacetophenone → HCID 86619548, compound

Participants

Reaction Steps

A THF solution (200 ml) containing t-butyl 4-bromobenzoate (19.9 g, 77.6 mmol), 4-chloroacetophenone (10 g, 64.7 mmol), Pd2dba3 (1.19 g, 1.29 mmol), BINAP (1.6 g, 2.58 mmol) and NaOtBu (8.7 g, 90.6 mmol) was refluxed under an argon atmosphere for approximately 5 hours. The solution was concentrated and then partitioned between EtOAc and water. The organic phase was washed with water, brine and dried over Na2SO4. The filtered solution was concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.95 (d, J=8.5 Hz, 2 H); 7.93 (d, J=8.7 Hz, 2 H); 7.43 (d, J=8.3 Hz, 2 H); 7.29 (d, J=8.2 Hz, 2 H); 4.30 (s, 2 H); 1.58 (s, 9 H). LC1 4.01 min. (M-tBu+H)=275

Provenance & Evidence