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

HRID 1255806Notes

Reaction equation

HRID 1255806 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.Cl[Sn]Cl.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

6

Reactant 3

HCID 243644-Bromo-2-nitrophenolHCID 24479Stannous ChlorideHCID 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 SnCl2 (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-8e0936efbe3a4cc184f5e65453179e60
Source dataset
uspto-grants-2013_06
Patent number
US08461157B2

Reaction notes

Loading…