Methyl Isobutyl Ketone → 1,1-Dichloro-2,2-bis(4-cyanatophenyl)ethylene

反応式

C(C(C)=O)C(C)C.[Cl:8][C:9]([Cl:25])=[C:10]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[N:26]#[C:27]Br.[CH2:29]([N:31](CC)CC)C>>[Cl:8][C:9]([Cl:25])=[C:10]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:27]#[N:26])=[CH:20][CH:19]=1)[C:11]1[CH:12]=[CH:13][C:14]([O:17][C:29]#[N:31])=[CH:15][CH:16]=1

参加物

反応物 4

HCID 7909Methyl Isobutyl Ketone

HCID 8471Triethylamine

HCID 10476Cyanogen Bromide

HCID 846771,1-Bis(4-hydroxyphenyl)-2,2-dichloroethylene

生成物 1

HCID 112212271,1-Dichloro-2,2-bis(4-cyanatophenyl)ethylene収率 98.2%

反応条件

温度: -20 °C

実験手順

A 4-necked 5-L flask, equipped with a mechanical stirrer, a thermometer, and an additional funnel, is charged with methyl isobutyl ketone (1500 g), 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethene (320 g), and cyanogen bromide (270 g). The resulting solution is cooled to −20° C. with a dry ice/acetone bath. To the stirring solution, triethylamine (240 g) in the additional funnel is added dropwise. The reaction temperature is maintained below −20° C. After the addition, the resulting mixture is allowed to warm up to 0° C. and quenched with dilute HCl aqueous solution. The organic layer is washed further with water a few times and concentrated under vacuum to afford 370 g of amber liquid, which solidifies as light tan color solids.