4-Bromo-3-nitrotoluene → 2-Bromo-5-methylaniline

HRID 1835525Notes

Reaction equation

HRID 1835525 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH2:9]

Participants

3

Reactant 2

HCID 792244-Bromo-3-nitrotolueneHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 64220652-Bromo-5-methylanilineYield 94.4%

Procedure

The title compound was prepared using the method of example 32, starting with 1-bromo-4-methyl-2-nitro-benzene (Lancaster, 10.1 g, 46.7 mmol), tin chloride dihydrate (Aldrich, 52.8 g, 233 mmol). 8.2 g (94%) of crude compound 244 was obtained as a pale brown oil.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-725acf4ab951495186d62b0c58c6720f
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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