Tin atom → 3-Bromo-5-chloro-2-methoxyaniline

HRID 1166226Notes

Reaction equation

HRID 1166226 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Br:11])[C:5]=1[O:12][CH3:13])([O-])=O.[Sn]>>[NH2:1][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Br:11])[C:5]=1[O:12][CH3:13]

Participants

3

Reactant 2

HCID 5352426Tin atomHCID 229976331-Bromo-5-chloro-2-methoxy-3-nitrobenzene

Product 1

HCID 162276703-Bromo-5-chloro-2-methoxyanilineYield 97.4%

Procedure

2-Amino-4-chloro-6-bromoanisole was prepared by the same procedure described for Step 3 of Preparation 2a except using 2-nitro-4-chloro-6-bromoanisole (16.2 g) and tin (14.5 g). Workup provided 2-amino-4-chloro-6-bromoanisole (14.0 g, 97%). 1H NMR (300 MHz, CDCl3) δ6.88 (d, J=2.4 Hz, 1H), 6.65 (d, J=2.4 Hz, 1H), 3.80 (s, 3H). 13C NMR (75 MHz, CDCl3) δ142.9, 141.9, 130.2, 121.4, 117.1, 114.6, 59.6.

Workup

  1. custom2-Amino-4-chloro-6-bromoanisole was prepared by the same procedure

Sources & evidence

ORD record
ord-8cb03e819c4c415c8d2073f2f33f3cc5
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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