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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1776337Generated: October 30, 2026

2-Nitroaniline → 4-Bromo-2-nitroaniline

https://huagongshe.com/reaction/1776337

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-NitroanilineHCID 6946—
ReactantN-bromobutanimideHCID 67184—
SolventAcetic AcidHCID 176—
SolventWaterHCID 962—
Product4-Bromo-2-nitroanilineHCID 7013276.3%

Reaction Conditions

Temperature40 °C

Reaction Steps

To a stirred solution of 2-nitroaniline (10.0 g, 72.462 mmol) in AcOH (50 mL) was added NBS (12.0 g, 72.463 mmol) at 0° C. under a N2 atmosphere. The reaction mixture was stirred at 40° C. for 30 min. After completion of starting material (monitored by TLC), reaction mixture was diluted with water and a white precipitate was formed. After filtration, the crude solid was recrystalised from n-hexanes to afford 4-bromo-2-nitroaniline (12 g, 76%), as a brown solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09265767B2
Source datasetuspto-grants-2016_02
ORD IDord-51dc99519b54443cbe781c6d1efebbbe
Source noteuspto-grants-2016_02