Hydrogen Bromide → Benzene, 1-bromo-3-nitro-

HRID 590374Notes

Reaction equation

HRID 590374 reaction equation
[BrH:1].[N+:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)N)([O-:4])=[O:3].CC1(C)N([O])C(C)(C)CCC1.N([O-])=O.[Na+].[OH-].[Na+]>O.C(#N)C>[Br:1][C:7]1[CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 74233-NitroanilineHCID 14798Sodium HydroxideHCID 2724126TempoHCID 23668193Sodium Nitrite

Product 1

HCID 11457Benzene, 1-bromo-3-nitro-Yield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

Water (45 ml), acetonitrile (6 ml), and 48% hydrobromic acid (27 ml) were added to 3-nitroaniline (2c) (2.76 g, 20 mmol) at room temperature. To the mixed solution, 2,2,6,6-tetramethylpiperidine 1-oxyl (0.31 g, 2 mmol) was added at room temperature, and the mixture was cooled to 10° C. or lower. Then, sodium nitrite (2.07 g) dissolved in water (15 ml) was added thereto. After stirring at room temperature for approximately 2 hours, a 10 mol/L aqueous sodium hydroxide solution (30 ml) was added thereto, and the precipitated crystals were collected by filtration, washed with water (40 ml), and then dried under reduced pressure to obtain 3-bromonitrobenzene (1c) (3.75 g, 93.0%). The instrumental spectrum data and HPLC retention time (Rt) of the obtained compound (1c) were completely consistent with those of the commercially available compound (1c).

Workup

  1. additionwas added
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water (40 ml)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d47f275727c64817b39dd080336100b6
Source dataset
uspto-grants-2016_01
Patent number
US09233980B2

Reaction notes

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