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

HRID 2200769Notes

Reaction equation

HRID 2200769 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-nitrophenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

As shown in step 6-iii of Scheme 6, to a solution of 2-amino-3-nitrophenol (5.00 g, 32.4 mmol) in dioxane (50 mL) was added bromine (6.22 g, 2.01 mL, 38.9 mmol). The mixture was stirred for 2 hours and a precipitate formed, which was collected and washed with dioxane and ether. The resulting yellow solid treated with a saturated NaHCO3 solution, which was extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 2-amino-5-bromo-3-nitrophenol (compound 1015) as a brown solid. This material was carried on as is in subsequent reactions without further purification.

Workup

  1. customa precipitate formed
  2. customwhich was collected
  3. washwashed with dioxane and ether
  4. additionThe resulting yellow solid treated with a saturated NaHCO3 solution, which
  5. extractionwas extracted with EtOAc (3×)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89d5441256a84eed93b1ed34e827ff9a
Source dataset
uspto-grants-2016_06
Patent number
US09359380B2

Reaction notes

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