Bromine → 2-Amino-5-bromo-3-nitrophenol

HRID 273538Notes

Reaction equation

HRID 273538 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[Br:12]Br>O1CCOCC1>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 598378212-Amino-5-bromo-3-nitrophenolYield 118.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

As shown by scheme (CLX), to a solution of 2-amino-3-nitrophenol 44 (10 g, 65 mmol) in anhydrous 1,4-dioxane (1 L) was added bromine (12.5 g, 78 mmol). The mixture was stirred at room temperature overnight. The solid was collected by filtration, washed with dioxane and dried. 2-amino-5-bromo-3-nitrophenol 45 (18 g, 90%) was obtained as its HBr salt in a form of a yellow solid. 1H NMR (DMSO-d6): δ 6.28 (br, 2H); 6.99 (d, J=2.2 Hz, 1H); 7.57 (d, J=2.1 Hz, 1H). MS (ESI+): m/z=234. Compound 45 (6 g, 19.1 mmol) was converted into compound 46 by using a method that was analogous to that used to synthesize compound 27, as shown on scheme (CXLI). Hydrogenation of compound 46 affords compound 47 (3.1 g, 67%) as a red solid.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with dioxane
  3. customdried

Sources & evidence

ORD record
ord-76b4f0809c4a4315b8551bba0789490b
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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