Sodium Carbonate → 3-Bromo-5-chlorobenzene-1,2-diamine

HRID 1024040Notes

Reaction equation

HRID 1024040 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH2:12].O.O.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 110648842-Bromo-4-chloro-6-nitrobenzenamine

Product 1

HCID 3515293-Bromo-5-chlorobenzene-1,2-diamineYield 97.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 109a (5.0 g, 20 mmol) in ethyl acetate (100 mL) was added SnCl2.2H2O (22.6 g, 100 mmol). The reaction was heated at reflux for 2 h. After cooled to room temperature, the reaction mixture was poured into aqueous Na2CO3 (200 mL) and the mixture was extracted with ethyl acetate (200 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 109b as a dark red liquid (4.3 g, 97%). LCMS: [M+H]+ 223. 1H NMR (500 MHz, CDCl3) δ 6.97 (d, J=2.5 Hz, 1H), 6.65 (d, J=2.5 Hz, 1H), 3.67 (bs, 4H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. extractionthe mixture was extracted with ethyl acetate (200 mL×3)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5b06d8aa67db4bca99eeb540054c84a1
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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