Hydrogen Bromide → 2-Bromo-3-nitrotoluene

A stirred solution of 2-methyl-6-nitroaniline (75.0 g, 0.493 mole) and 40 ml of hydrobromic acid (48% solution) in 135 ml of water was cooled to 0°. During a one hour period a solution of sodium nitrite (36.2 g, 0.51 mole) in 60 ml of water was added to the reaction mixture. The mixture was suction filtered through a sintered glass funnel, collecting the filtrate in a flask cooled by a dry ice-acetone bath. The filtrate was placed in a jacketed addition funnel cooled by a dry ice-acetone bath. During a five minute period this solution was added to a stirred mixture of cuprous bromide (77.8 g, 0.51 mole) in 165 ml of hydrobromic acid (48% solution). After complete addition, the mixture was stirred at room temperature for approximately 18 hours, heated at reflux for two hours, then steam distilled. The distillate was extracted with methylene chloride and the extract washed with 2N aqueous sodium hydroxide, followed by several portions of saturated aqueous sodium chloride solution. The organic phase was passed through phase separation filter paper and evaporated under reduced pressure to give 1-bromo-2-methyl-6-nitrobenzene (17 g) as a solid.

1. filtrationfiltered through a sintered glass funnel
2. customcollecting the filtrate in a flask
3. temperaturecooled by a dry ice-acetone bath
4. customThe filtrate was placed in a jacketed addition funnel
5. temperaturecooled by a dry ice-acetone bath
6. additionAfter complete addition
7. temperatureheated
8. temperatureat reflux for two hours
9. distillationsteam distilled
10. extractionThe distillate was extracted with methylene chloride
11. washthe extract washed with 2N aqueous sodium hydroxide
12. customThe organic phase was passed through phase separation
13. filtrationfilter paper
14. customevaporated under reduced pressure

ORDレコード

ord-32c6a7f4c36a44a497c6416818099cf4

出典データセット

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04536591