5-Bromo-1-methoxy-2-methyl-3-nitrobenzene → 5-Bromo-3-methoxy-2-methylaniline

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([CH3:10])=[C:6]([O:8][CH3:9])[CH:7]=1.ClC1C(B2OC(C)(C)C(C)(C)O2)=CC=CC=1N>>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[C:4]([CH:3]=1)[NH2:11]

Participants

Reactant 2

HCID 247281025-Bromo-1-methoxy-2-methyl-3-nitrobenzene

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

Product 1

HCID 272747255-Bromo-3-methoxy-2-methylaniline

Procedure

This material was prepared from 5-bromo-1-methoxy-2-methyl-3-nitrobenzene following the procedure used for SM-9, step 2: LCMS (m/z): 216.0 (MH+); tR=0.65 minute.

Sources & evidence

ORD record: ord-f18abec1e79f489897427bbdd4bd52a7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563553B2

Reaction notes

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