Ethyl Acetate → 2-Amino-4-Bromophenol

HRID 2116701Notes

Reaction equation

HRID 2116701 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-1578bc8b243c4a488b45da642702732c
Source dataset
uspto-grants-2008_10
Patent number
US07439236B2

Reaction notes

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