Water → 2-Bromo-3,4-dimethylaniline

HRID 1784522Notes

Reaction equation

HRID 1784522 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.O.O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 8259382-Bromo-3,4-dimethyl-1-nitrobenzene

Product 1

HCID 668731062-Bromo-3,4-dimethylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-3,4-dimethylnitrobenzene (1.0 g, 4.35 mmole) in 10 mL DMF was added SnCl2.2H2O (4.92 g, 21.8 mmole). This solution was stirred overnight at room temperature 50 mL of H2O was added and the pH was adjusted to 8 with the addition of sat. NaHCO3 and extracted with 150 mL of EtOAC. The organic layer was dried over Na2SO4, filtered and evaporated yielding 2-bromo-3,4-dimethylaniline which was used as is in the conversion to 2-bromo-3,4-dimethyliodobenzene in a similar manner to that of Example 86. Compound 102 was prepared from 2-bromo-3,4-dimethyliodo-benzene using procedures similar to those of Examples 25 and 40. MS (ion spray): m/z 314.0/316.1 (M−H); 316.1/318.0 (M+H). 1H NMR: (DMSO-d6, 400 MHz) δ 7.37 (d, 1H), 7.15 (d, 1H), 2.43 (s, 3H), 2.37 (s, 3H).

Workup

  1. additionwas added
  2. extractionextracted with 150 mL of EtOAC
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bacd7e94c6644747b69497e12a174d52
Source dataset
uspto-grants-2009_03
Patent number
US07504389B2

Reaction notes

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