Hydrogen Bromide → 4-Bromo-1-ethyl-2-nitrobenzene

温度

-5 °C

Hydrobromic acid (48% wt. in water, 240 ml) is added dropwise to a suspension of 4-ethyl-3-nitroaniline (20 g, 0.12 mol) in water (80 ml), and the mixture is stirred until the solid dissolves. The mixture is cooled to −5° C. and a solution of sodium nitrite (19.8 g, 0.28 mol) in water (100 ml) is added dropwise, maintaining the temperature at 0-5° C. Once the addition is complete, the cooling bath is removed and the reaction mixture is stirred for one hour at room temperature. The mixture is added dropwise to a pre-cooled solution of cuprous bromide (22.4 g, 0.16 mol) in hydrobromic acid (48% wt. in water) at 0° C. The reaction mixture is stirred and allowed to warm to room temperature over three hours. The mixture is extracted with diethyl ether, and the organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with hexane to give 4-bromo-1-ethyl-2-nitrobenzene (18 g)

1. dissolutiondissolves
2. temperaturemaintaining the temperature at 0-5° C
3. additionOnce the addition
4. customthe cooling bath is removed
5. stirringthe reaction mixture is stirred for one hour at room temperature
6. stirringThe reaction mixture is stirred
7. temperatureto warm to room temperature over three hours
8. extractionThe mixture is extracted with diethyl ether
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationthe filtrate is concentrated in vacuo
12. customThe residue is further purified by column chromatography on silica gel
13. washeluting with hexane

ORDレコード

ord-926cf9a3af704445bf194814e73ac693

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530388B2