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

HRID 2427200Notes

Reaction equation

HRID 2427200 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-e0af6cf7bdeb4c28b8611fadc6597a0c
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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