Tetrahydrofuran → 2-Bromo-N-(2-hydroxy-5-nitro-phenyl)-2-methyl-propionamide

HRID 238476Notes

Reaction equation

HRID 238476 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C1COCC1.[Br:17][C:18]([CH3:23])([CH3:22])[C:19](Br)=[O:20]>CCN(CC)CC>[Br:17][C:18]([CH3:23])([CH3:22])[C:19]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11])=[O:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 886852-Bromo-2-methylpropionyl bromideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 105663292-Bromo-N-(2-hydroxy-5-nitro-phenyl)-2-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Amino-4-nitro-phenol (3.08 g, Aldrich) was stirred with THF (30 ml, Aldrich) in an ice bath. 2-Bromo-2-methyl-propionyl bromide (2.47 ml, Aldrich) and Et3N (2.0 g, Aldrich) was slowly added via syringe. The mixture was stirred for 45 min then poured into ice. The aqueous phase was extracted by EtOAc (50 mL×4). The organic layer was dried and concentrated. The desired product was crystallized from EtOAc. (Chem. Pharm. Bull 1996, 44(1) 103-114).

Workup

  1. additionthen poured into ice
  2. extractionThe aqueous phase was extracted by EtOAc (50 mL×4)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe desired product was crystallized from EtOAc

Sources & evidence

ORD record
ord-e9c7bef1e21b4e8ca2acd506ea6128ce
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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