On the Kolbe—Schmitt Reaction

5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2

“…Prepared using general method 5.3 from 3-formyl-2-hydroxybenzonitrile (0.34 g, 1.7 mmol) 29 . White solid (0.48 g, 94%).…”

“…Prepared using general method 5.3 from 3-formyl-2-hydroxybenzonitrile (0.34 g, 1.7 mmol). 29 White solid (0.48 g, 94%). Mp 84–86 °C; 1 H NMR: δ 2.46 (3H, s, Me), 7.55 (2H, d, J = 8.5 Hz, Ph 3-H), 7.75 (1H, t, J = 7.6 Hz, C5-H), 7.82 (2H, d, J = 8.5 Hz, Ph 2-H), 8.15 (1H, dd, J = 1.8, 7.6 Hz, C6-H), 8.28 (1H, dd, J = 1.8, 7.6 Hz, C4-H), 9.84 (1H, s, CHO); 13 C NMR: δ 21.76 (CH 3 ), 109.73 (Cq), 114.46 (Cq), 129.27 (CH), 129.55 (CH), 129.95 (Cq), 131.22 (Cq), 131.25 (CH), 133.78 (CH), 140.01 (CH), 148.06 (Cq), 150.68 (Cq), 186.55 (CH).…”

“… 28 3-Formyl-2-hydroxybenzonitrile was obtained by Reimer-Tiemann ortho -formylation of 2-hydroxybenzonitrile. 29 …”

An Improved Method for the Synthesis of 3-Fluorosalicylic Acid with Application to the Synthesis of 3-(Trifluoromethyl)salicylic Acid

“…This compound was prepared in 85% yield according to the procedure described for 3-fluorosalicylic acid (4). An analytical sample was prepared by flash column chromatography on silica gel using 0.5% HOAc in CHCl 3 as the eluent.…”

“…3-Fluorosalicylic acid (4) has also been prepared in low yield through Kolbe-Schmitt carbonation of 2-fluorophenol. 2,4 Recently, a method has been reported for the synthesis 3,5-difluorosalicylic acid from 2,4-difluorophenol via a Duff reaction, which involves the formation of an aromatic aldehyde via formylation using hexamethylenetetramine (HMT). 5 A modification of this procedure employing a positional protective group strategy 6 has led to the synthesis outlined in Scheme 1.…”