1-Bromo-2,5-dichloro-3-nitrobenzene → 3-Bromo-2,5-dichloroaniline

HRID 535735

Reaction equation

HRID 535735 reaction equation
ClC1C(B2OC(C)(C)C(C)(C)O2)=CC=CC=1N.[Br:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([N+:26]([O-])=O)[C:20]=1[Cl:29]>>[Br:18][C:19]1[C:20]([Cl:29])=[C:21]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[NH2:26]

Participants

3

Reactant 2

HCID 183545541-Bromo-2,5-dichloro-3-nitrobenzeneHCID 581644322-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

Product 1

HCID 183545303-Bromo-2,5-dichloroanilineYield 24%

Procedure

This material was prepared according to the procedure used for SM-9, step 2 using 1-bromo-2,5-dichloro-3-nitrobenzene. Purification by flash chromatography (SiO2, 0-30% EtOAc in heptane) provided 3-bromo-2,5-dichloroaniline (24%): LCMS (m/z) 239.9 (MH+), tR=1.03 minutes; 1H NMR (400 MHz, CDCl3) δ 4.28 (br s, 2H) 6.71 (d, J=2.4 Hz, 1H) 7.02 (d, J=2.4 Hz, 1H).

Workup

  1. customThis material was prepared
  2. customPurification by flash chromatography (SiO2, 0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-ceb7cc0e12d944d29c0c532bb9096bf1
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Linked notes

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