Ethyl Acetate → 2-Amino-4-Bromophenol

HRID 1815753Notes

Reaction equation

HRID 1815753 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(OCC)(=O)C>O>[NH2:11][C:6]1[CH:5]=[C:4]([Br:3])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 243644-Bromo-2-nitrophenolHCID 24489Sodium Dithionite

Product 1

HCID 3518402-Amino-4-BromophenolYield 56.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of KOH (5.14 g, 91.7 mmol) in water (33 mL) was added to 4-bromo-2-nitrophenol (Aldrich, 1.00 g, 4.59 mmol). Sodium hydrosulfite (7.98 g, 45.9 mmol) was added in one portion. The mixture was stirred at RT for 30 min. and poured into ethyl acetate (25 mL). The layers were partitioned and the aqueous layer was extracted with ethyl acetate (4×25 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to give 488 mg (56%) of the title compound which was used without further purification: 1H NMR (CDCl3, 400 MHz) δ 6.77 (d, 1H, J=2.1 Hz), 6.65 (dd, 1H, J=8.3, 2.5 Hz), 6.52 (d, 1H, J=8.3 Hz); 13C NMR (CDCl3, 100 MHz) δ 144.0, 136.6, 121.7, 118.7, 116.2, 112.1; MS (Cl) m/z 188.0 (M+1); HPLC retention time=1.10 min.

Workup

  1. customThe layers were partitioned
  2. extractionthe aqueous layer was extracted with ethyl acetate (4×25 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40b741b99ed74fd6820aa388fb822b9f
Source dataset
uspto-grants-2005_04
Patent number
US06881734B2

Reaction notes

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