Ethanol → 1-(4-Amino-2-chlorophenoxy)-2-bromoethane

HRID 1106870Notes

Reaction equation

HRID 1106870 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][Br:7].C(O)C.[O-]S(S([O-])=O)=O.[Na+].[Na+]>O>[NH2:12][C:10]1[CH:9]=[CH:8][C:3]([O:4][CH2:5][CH2:6][Br:7])=[C:2]([Cl:1])[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 3099731-(2-bromoethoxy)-2-chloro-4-nitrobenzene

Product 1

HCID 187898501-(4-Amino-2-chlorophenoxy)-2-bromoethaneYield 23.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 11 g (0.040 mol) of the 1-(2-chloro-4-nitrophenoxy)-2-bromoethane produced in Example 5-(1), ethanol (170 ml) was added and dissolved therein; to the resulting solution, Na2S2O4 (27.6 g, 0.158 mol) as dissolved in water (50 ml) was added dropwise, followed by stirring at room temperature for 20 min. The solvent was evaporated and the residue was diluted with an aqueous solution of sodium bicarbonate and two extractions were conducted with ethyl acetate. The organic extracts were dried with sodium sulfate and the solvent was evaporated, with the residue being purified by being subjected to column chromatography on silica gel using, as an eluent, n-hexane containing ethyl acetate (25%) to yield the end compound 1-(4-amino-2-chlorophenoxy)-2-bromoethane (2.35 g) as a pale yellow solid mass.

Workup

  1. dissolutiondissolved
  2. additionwas added dropwise
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with an aqueous solution of sodium bicarbonate and two extractions
  5. dry with materialThe organic extracts were dried with sodium sulfate
  6. customthe solvent was evaporated, with the residue
  7. custombeing purified
  8. additionn-hexane containing ethyl acetate (25%)

Sources & evidence

ORD record
ord-a18f57c282a24535b0600d15ce670401
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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