Hydrochloric Acid → 3-Bromo-2-methoxyaniline

HRID 513230Notes

Reaction equation

HRID 513230 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[O:11][CH3:12].Cl[Sn]Cl.Cl>C1COCC1>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 225057131-Bromo-2-methoxy-3-nitrobenzene

Product 1

HCID 226677353-Bromo-2-methoxyaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-Bromo-2-methoxy-3-nitro-benzene (17.8 g, 0.0768 mol), SnCl2 (69.27 g, 0.3069 mol) and 4N HCl (80 mL) in THF (200 mL) is stirred at 80° C. for 16 h. After reaction, evaporated out THF and added NaHCO3 solution, filtered and the filtrate is extracted with ethyl acetate (3×800 mL). The combined organic phase is ished with water and brine, dried over Na2SO4, concentrated in vacuo to give the desired product. Yield: 14.8 g (96%).

Workup

  1. customAfter reaction
  2. customevaporated out THF
  3. additionadded NaHCO3 solution
  4. filtrationfiltered
  5. extractionthe filtrate is extracted with ethyl acetate (3×800 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c8d770a6f074fd3a318c0d5e69c5ee3
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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