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

HRID 1790198Notes

Reaction equation

HRID 1790198 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 Hz, 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-c72610874ea448b4a4768ec392bc794b
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

Loading…