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

HRID 887551Notes

Reaction equation

HRID 887551 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 compound 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 compound was crystallized from EtOAc (Chem. Pharm. Bull 1996, 44(1) 103-114)

Sources & evidence

ORD record
ord-4d8fb17150d94753819df679cc50728d
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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