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

HRID 1270098Notes

Reaction equation

HRID 1270098 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 without further purification.

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-2e7b3b9902d947de8c2f47c251c6b96c
Source dataset
uspto-grants-2007_04
Patent number
US07202241B2

Reaction notes

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