Water → HCID 49766558, compound

HRID 1941971Notes

Reaction equation

HRID 1941971 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-0e15a21070b74bb3976c6ebc483fe477
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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