Ammonium Acetate → 1-Methyl-2-(2,4,6-tribromo-phenoxy)-ethylamine

HRID 2189961Notes

Reaction equation

HRID 2189961 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([Br:14])[C:3]=1[O:4][CH2:5][C:6](=O)[CH3:7].C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[CH3:7][CH:6]([NH2:21])[CH2:5][O:4][C:3]1[C:2]([Br:1])=[CH:12][C:11]([Br:13])=[CH:10][C:9]=1[Br:14]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 33030042,4,6-TribromophenoxyacetoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 452831771-Methyl-2-(2,4,6-tribromo-phenoxy)-ethylamineYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g 1-(2,4,6-tribromo-phenoxy)-propan-2-one (2.6 mmol) in 20 ml methanol is added 2.9 g ammonium acetate (39 mmol). The mixture is cooled to 0° C. and 0.81 g sodiumcyanoborohydride (13 mmol) is added. The reaction mixture is stirred overnight at ambient temperature. The completion of the reaction is confirmed by TLC. The reaction mixture is concentrated and the remaining residue is dissolved with 1.5 N HCl and washed with diethylether. The aqueous layer is neutralised and extracted with ethylacetate. The ethylacetate layer is dried over anhydrous sodium sulphate and the solvent removed. 0.32 g 1-methyl-2-(2,4,6-tribromo-phenoxy)-ethylamine (32%) is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionthe remaining residue is dissolved with 1.5 N HCl
  3. washwashed with diethylether
  4. extractionextracted with ethylacetate
  5. dry with materialThe ethylacetate layer is dried over anhydrous sodium sulphate
  6. customthe solvent removed

Sources & evidence

ORD record
ord-a0968f2ae70d429b94778511187801b7
Source dataset
uspto-grants-2012_12
Patent number
US08324263B2

Reaction notes

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