1,2-Dibromoethane → 5-Bromo-2-(2-bromoethoxy)aniline

HRID 383264Notes

Reaction equation

HRID 383264 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:12][CH2:11][Br:10])=[C:2]([NH2:1])[CH:7]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3518402-Amino-4-Bromophenol

Product 1

HCID 669776445-Bromo-2-(2-bromoethoxy)anilineYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product 2-amino-4-bromophenol (500 mg, 2.66 mmol), 1,2-dibromoethane (2.5 g, 13.3 mmol) and K2CO3 (1.84 g, 13.3 mmol) in DMF (10 mL) was stirred at room temperature for 4 h. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (3×50 mL) and brine (50 mL), concentrated and purified by column chromatography on silica gel (ethyl acetate in petroleum, 10% v/v) to give 5-bromo-2-(2-bromoethoxy)benzenamine (250 mg, 37%) as a yellow solid. LCMS: 294 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 3.79 (t, J=6.0 Hz, 2H), 4.25 (t, J=5.6 Hz, 2H), 5.06 (s, 2H), 6.63 (dd, J1=2.4 Hz, J2=8.0 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with water (3×50 mL) and brine (50 mL)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (ethyl acetate in petroleum, 10% v/v)

Sources & evidence

ORD record
ord-d4d6425292714c3baff81e2eaa12c49e
Source dataset
uspto-grants-2013_02
Patent number
US08367663B2

Reaction notes

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