1,3-Dibromo-5,5-dimethylhydantoin → 4-Bromo-2-chloro-5-methoxyaniline

HRID 1897565Notes

Reaction equation

HRID 1897565 reaction equation
[Br:1]N1C(C)(C)C(=O)N(Br)C1=O.[Cl:12][C:13]1[C:18]([NH2:19])=[CH:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Br:1][C:15]1[C:16]([O:20][CH3:21])=[CH:17][C:18]([NH2:19])=[C:13]([Cl:12])[CH:14]=1

Participants

6

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 11430Potassium CarbonateHCID 754606-Chloro-m-anisidine

Product 1

HCID 147747824-Bromo-2-chloro-5-methoxyanilineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

1,3-Dibromo-5,5-dimethylhydantoin (commercially available, for example, from Aldrich) (9.1 g, 32 mmol) was added over 20 minutes to a stirred solution of 6-chloro-3-methoxyaniline (commercially available, for example, from Apollo Scientific) (10.0 g, 63 mmol) in ethyl acetate (150 ml) at −5° C. The resulting solution was stirred at −5° C. for 1 hour then washed with a solution of potassium carbonate (6 g, 43 mmol) in water (40 ml and then with water (20 ml). The resulting solution was concentrated under reduced pressure to give 4-bromo-2-chloro-5-methoxyaniline as a pale brown solid (14.3 g, 95%).

Workup

  1. customat −5° C
  2. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5011efe559c4d05b6a1a6eb032dc6e7
Source dataset
uspto-grants-2013_08
Patent number
US08519138B2

Reaction notes

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