N-bromobutanimide → 4-Bromo-5-chloro-2-nitroaniline

HRID 475276Notes

Reaction equation

HRID 475276 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.C1C(=O)N([Br:19])C(=O)C1>CC(O)=O>[Br:19][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([NH2:8])=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 218469994-Bromo-5-chloro-2-nitroanilineYield 46.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-2-nitrobenzenamine (6.0 g, 34.9 mmol) and NBS (6.06 g, 34.0 mmol) in HOAc (240 mL) was heated at 110° C. for 1 h. The solution was cooled to RT and the reaction mixture was poured into an ice-water (800 mL). The resulting solid was filtered, washed with water (50 mL×3), and dry under vacuum to afford 4.0 g (44%) of 4-bromo-5-chloro-2-nitrobenzenamine (246) as yellow solid: MS (ESI) m/z=250.9 (M−1).

Workup

  1. temperatureThe solution was cooled to RT
  2. filtrationThe resulting solid was filtered
  3. washwashed with water (50 mL×3)
  4. customdry under vacuum

Sources & evidence

ORD record
ord-966e0e56f6a341f3874b04425deb24ba
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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