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

HRID 383263Notes

Reaction equation

HRID 383263 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-c38e6cc82a00442093a2e29ec3a8a771
Source dataset
uspto-grants-2013_02
Patent number
US08367663B2

Reaction notes

Loading…