Hydrochloric Acid → 4-Bromo-3'-nitrobenzophenone

反応式

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:8])=[CH:16][CH:15]=1

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 7961Bromobenzene

HCID 8495Benzoyl chloride, 3-nitro-

HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 123219594-Bromo-3'-nitrobenzophenone収率 91.7%

反応条件

温度: 100 °C

実験手順

In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser were placed 3-nitrobenzoyl chloride (28 g, 0.15 mol), bromobenzene (130 g, 0.83 mol), and aluminum chloride (22 g, 0.16 mol). The mixture was heated for 3 h at 100° C., then cooled to room temperature and stirred for an additional 16 h. The mixture was poured into 1 L of acidic (HCl) ice water, and the organics were extracted using methylene chloride, dried over magnesium sulfate, and the solvents were removed under reduced pressure to yield a yellow powder. Recrystallization from acetone afforded 42.1 g (90% yield) of white crystals: m.p. 104°-105° C.