2,3-Difluorobenzoyl chloride → HCID 58923398, compound

Participants

Reaction Conditions

Reaction Steps

Aluminum chloride (905 mg, 6.79 mmol) was added to a solution of 5-morpholin-4-yl-benzene-1,3-diol in nitrobenzene (8 mL), and the mixture was heated to 110° C. A solution of 2,3-difluorobenzoyl chloride in nitrobenzene was added slowly, and the mixture was heated at 100° C. for 12 h. The majority of the nitrobenzene was removed via short-path vacuum distillation. The black residue was dissolved in water/EtOAc (1:1, 20 mL). The aqueous component was extracted with EtOAc (3×40 mL), and the combined extracts were dried (MgSO4) and filtered through a ¾-inch silica gel plug. The filtrate was concentrated and purified via Biotage chromatography (100% hexanes to 30% EtOAc/hexanes) to yield 196 mg (22%) of (2,3-difluorophenyl)-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)methanone. 1H NMR (CDCl3, 400 MHz) δ: 7.30-7.10 (comp., 3H), 5.85 (s, 2H), 3.85-3.75 (m, 4H), 3.42-3.38 (m, 4H).

Provenance & Evidence