Hydrogen Bromide → 1-Bromo-2-isopropyl-4-nitrobenzene
Reaction equation
N([O-])=O.[Na+].[CH:5]([C:8]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=1N)([CH3:7])[CH3:6].[BrH:18]>O>[CH:5]([C:8]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=1[Br:18])([CH3:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 7.5 g of sodium nitrite in 20 ml of water was added at -20° C. to 0° C. over 20 minutes to a suspension of 18.5 g of the product of Step C, 120 ml of a 48% hydrobromic acid solution and 80 ml of water and the mixture was stirred at 0° C. for 15 minutes and kept thereafter at 0° C. A solution of 22 g of cuprous bromide in 80 ml of 48% hydrobromic acid solution was heated with stirring to 50°-55° C. and the previous solution was then added thereto. The mixture was stirred at 55°-60° C. for one hour, was cooled and poured into water. The mixture was extracted with methylene chloride and the combined organic phases were washed with N sodium hydroxide solution, with water, dried and evaporated to dryness under reduced pressure at 50° C. The residue was rectified under reduced pressure to obtain 20.4 g of 3-isopropyl-4-bromo-nitrobenzene with a boiling point of 150°-152° C. at 8 mm Hg and having a refractive index of nD22 =1.5775.
Workup
- customat 0° C
- stirringwith stirring to 50°-55° C.
- additionthe previous solution was then added
- stirringThe mixture was stirred at 55°-60° C. for one hour
- temperaturewas cooled
- extractionThe mixture was extracted with methylene chloride
- washthe combined organic phases were washed with N sodium hydroxide solution, with water
- customdried
- customevaporated to dryness under reduced pressure at 50° C
Sources & evidence
- ORD record
- ord-3d479b1f8cc244c5bdca1e48253b8524
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801717
Reaction notes
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