反应详情

To 105 mg (0.244 mmol) of 18 suspended in 15 mL of dry methanol, was added 61 mg (0.268 mmol) of dichlorodicyanobenzoquinone (DDQ) and the reaction left to stir at room temperature for 1 hour. The solids were filtered off, washed with methanol, and dried to afford pure 19: 95 mg (91%) yield; dec pt 274°-275° C.; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.46; IR (KBr pellet) 3062, 3040, 2990, 2933, 1713, 1645, 1576, 1547, 1480, 1142 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ4.45 (4H, s, methylenes); mass spectrum (EI, solids probe), m/z 428, 430, and 432 (P+ for the 79Br, 79Br; 79Br, 81Br, 81Br, 81Br combinations, respectively, in an intensity ratio of 1:2:1). Anal. Calcd for C12H6Br2N4O4 ; C, 33.52; H, 1.41; N, 13.03. Found: C, 33.89; H, 1.31; N, 12.50.

1. waitthe reaction left
2. filtrationThe solids were filtered off
3. washwashed with methanol
4. customdried
5. customto afford pure 19
6. custom95 mg (91%) yield