5-Bromosalicylaldehyde → 2-Hydroxy-5-(2-thienyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

The synthesis of this compound is depicted schematically in FIG. 13. To a mixture of 5-bromosalicylaldehyde (2.847 g, 14.16 mmol) and Cl2Pd(PPh3)2 (0.497 g, 0.708 mmol, 0.05 equiv) was added tributylstannyl thiophene (6.75 mL, 21.24 mmol, 1.5 equiv) in 25 mL of DMF. The reaction mixture was heated at 80° C. 16 h, over which time the reaction color changed from light yellow to dark red. The reaction was cooled, diluted with Et2O and washed with dilute NH4Cl (4×150 mL). The organic layer was collected and filtered through a short silica pad to yield a yellow filtrate. The solvent was removed under reduced pressure to afford a gummy yellow solid, which was transferred to a frit and washed with hexanes. The yellow solid was dried in vacuo to afford 1.895 g (9.28 mmol, 66%) of a yellow powder (mp 102-103° C.). 1H NMR (CDCl3) δ11.01 (s, 1H), 9.96 (s, 1H), 7.80-7.76 (m, 2H), 7.29-7.24 (m, 2H), 7.11-7.07 (dd, 1H), 7.05-7.02 (dd, 1H). 13C NMR (CDCl3) δ196.5, 161.1, 142.7, 134.7, 130.8, 128.3, 127.1, 124.8, 123.0, 120.8, 118.4. MS m/z (204 (M+). HRMS (FAB) found m/z 205.0324 (M+H+); calcd for C11H9O2S m/z 205.0323 (M+H+).

Provenance & Evidence