Pentafluorobenzyl bromide → 3',5'-Di[(pentafluorobenzyl)oxy]acetophenone

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Reaction Steps

Synthesized by 1:2 ratio of 3',5'-dihydroxyacetophenone to pentafluorobenzyl bromide. Yield: 98%. m.p. 102°-103° C. 1H NMR, δ: 2.60 (s, 3H, CH3CO), 5.22 (s, 4H, CH2O), 6.83 (bs, 1H, H-C4'), 7.24 (d, 2H, J=1.8 Hz, H-C2' & H-C6') ppm; 13C NMR, δ: 26.0 (CH3CO), 57.4 (CH2O), 106.4 (C4'), 107.4 (C2' & C6'), 109.7 (C1", 2JC-F =17 Hz) 137.4 (C2" & C6", JC-F =249 Hz), 139.2 (C1'), 141.7 (C4", JC-F =256 Hz), 145.7 (C3" & C5", JC-F =251 Hz), 159.2 (C3' & C5'), 196.7 (C=O) ppm. MS(EI): 331 ([M-PFBz]+); MS(ECNI): 331 ([M-PFBz]-, 100%).

Provenance & Evidence