Water → HCID 49766558, compound

HRID 447050Notes

Reaction equation

HRID 447050 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[Br:12]Br.O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:12])=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 49766558HCID 49766558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 2-amino-5-nitro phenol (40.0 g, 259.52 mmol) in DCM (1.0 L), was added bromine (13.38 mL, 259.52 mmol) drop wise. The resulting reaction mixture was stirred at room temperature for 45 min. After the completion of the reaction (TLC monitoring), water was added and extracted with EtOAc (3×1.0 L). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude (55.0 g, 92%) was carried forward to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. extractionextracted with EtOAc (3×1.0 L)
  4. dry with materialThe combined organics was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude (55.0 g, 92%) was carried forward to the next step without further purification

Sources & evidence

ORD record
ord-ccc715c7f9624efbb093031d5b468986
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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