Ethanol → Benzenamine, 3-bromo-4-methyl-

HRID 915187Notes

Reaction equation

HRID 915187 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:11].C(O)C.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH3:11])[NH2:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 821892-Bromo-4-nitrotoluene

Product 1

HCID 82187Benzenamine, 3-bromo-4-methyl-Yield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-4-nitrotoluene (50 g, 0.231 mol in ethylacetate (330 mL) and Ethanol (150 mL) was added Tin(II)chloride dihydrate (208 g, 0.924 mol) portionwise. The reaction mixture was stirred at room temperature overnight. The solution was then treated with potassium carbonate until pH=7 and filtered over celite. The filtrate was washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 42.71 g (100%) of 3-bromo-4-methylaniline. 1H NMR (300 MHz; CDCl3): 2.27 (s, 3 H), 3.57 (br s, 2 H), 6.54 (dd, J=2.7 Hz and 8.1 Hz, 1 H), 6.90 (d, J=2.1 Hz, 1 H), 6.98 (d, J=8.1 H).

Workup

  1. filtrationfiltered over celite
  2. washThe filtrate was washed with water, aqueous NaHCO3, water and brine
  3. dry with materialdried (Mg2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dcd8769e642743acbd3e171f7fe5b573
Source dataset
uspto-grants-2007_09
Patent number
US07265139B2

Reaction notes

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