4-Bromo-2-nitrophenol → 2-Amino-4-Bromophenol

HRID 1399933Notes

Reaction equation

HRID 1399933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.C([O-])(O)=O.[Na+]>C(O)C.O>[NH2:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

5

Reactant 2

HCID 243644-Bromo-2-nitrophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 3518402-Amino-4-BromophenolYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of compound 4-bromo-2-nitrophenol (1 g, 4.59 mmol) and 5 nCl2 (5.2 g, 22.9 mmol) in ethanol (10 mL) was stirred at 70° C. for 2 h. After cooled down, the mixture was diluted with water (100 mL), adjusted to pH 7 with saturated aqueous NaHCO3 and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4, concentrated to give 2-amino-4-bromophenol (770 mg, 89%) as a grey solid. LCMS: 188 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 4.79 (s, 2H), 6.48 (dd, J1=2.4 Hz, J2=8.4 Hz, 1H), 6.55 (d, J=8.4 Hz, 1H), 6.71 (d, J=2.4 Hz, 1H), 9.26 (s, 1H).

Workup

  1. temperatureAfter cooled down
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2edd157261ee4d4aba38424355686f4c
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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