Water → 2-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamide

HRID 723312Notes

Reaction equation

HRID 723312 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15].[Br:16][C:17]([CH3:22])([CH3:21])[C:18](Br)=[O:19].O>C(Cl)Cl>[Br:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 886852-Bromo-2-methylpropionyl bromideHCID 155315062-Amino-6-bromophenol

Product 1

HCID 218735182-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (1.8 ml, 22.3 mmol) was added to a solution of 2-Amino-6-bromo-phenol (4.198 g, 22.3 mmol) in dry CH2Cl2 (200 ml). The mixture was cooled in ice and then a solution of 2-bromo-2-methyl-propionylbromide (2.8 ml, 22.6 mmol) was added slowly. The mixture was stirred at the room temperature for an hour and was poured into CH2Cl2 and water. The organic layer was washed with water, dried and concentrated in vacuo to yield crude 2-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamide, which was used directly in step 2.

Workup

  1. temperatureThe mixture was cooled in ice
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da887553a4e74faebce16e987dc52703
Source dataset
uspto-grants-2006_11
Patent number
US07141562B2

Reaction notes

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