Dimethylformamide → 2,3,4,5-Tetrafluorobenzoyl chloride

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Reaction Steps

A mixture of 25 g (130 mmol) 2,3,4,5-tetrafluorobenzoic acid, 0.5 ml DMF, 200 ml CH2Cl2 and 17 ml (192 mmol) oxalyl chloride was stirred at room temperature for 21 hours. The mixture was filtered and evaporated in vacuo. The concentrate was extracted with 3×300 ml hexane. The extract was filtered via gravity through a coarse pore sintered glass funnel. This filtrate was evaporated in vacuo to yield 22 g (76%) of 2,3,4,5-tetrafluorobenzoylchloride as a colorless liquid. 1H-NMR(CDCl3) δ281-289 (m, 1H); 13C-NMR(CDCl3): δ114.882 (d, J=21.7 Hz), 141.300 (d, J=270.0 Hz), 144.763 (d, J=279 Hz), 146.303 (d, J=241 Hz), 147.595 (d, J=279 Hz), 160.593.

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