4-(Dimethylamino)Benzaldehyde → 4-Dimethylamino-3'-fluorobenzoin

反応式

[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[C-]#N.[K+]>C(O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]([CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=2)[OH:17])=[O:8])=[CH:5][CH:4]=1

参加物

実験手順

A mixture consisting of 14.9 g. of p-dimethylaminobenzaldehyde, 12.4 g. of m-fluorobenzaldehyde, 6 g. of potassium cyanide, and 100 ml. of 65% ethanol is reacted according to the procedure of Example 20, 12.8 g. of 4-dimethylamino-3'-fluorobenzoin being obtained; m.p. 147°-149° C. An 8.2 g. portion of this benzoin is converted to its methanesulfonate ester, by the procedure of Example 20, in 9.1 g. yield, m.p. 106°-109° C. A mixture of 2.6 g. of the methanesulfonate ester, 0.91 g. of hexahydro-2H-1,3-diazepin-2-thione, and 70 ml. of acetone is left at room temperature for three days, precipitating the title compound in 2.7 g. yield, m.p. 180°-182° C.