4-Nitrophenol → 1-(2-Bromoethoxy)-4-nitrobenzene

HRID 2249577Notes

Reaction equation

HRID 2249577 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11][CH2:12][CH2:13]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:12][Br:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneYield 32%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitrophenol (1.0 g, 1.0 eq., 7.19 mmol), 1,2-dibromoethane (3.85 mL, 6.0 eq, 43.1 mmol), and anhydrous K2CO3 (3.0 g, 3 eq, 21.5 mmol) in dry acetone (36 mL) was stirred at RT for 16 h. The reaction mixture was filtered, and the filtrate was condensed. Condensed mass was again dissolved in ethyl acetate and washed with aq. sodium bicarbonate solution. Organic layer was dried (Na2SO4), condensed, and the residue was chromatographed using ethyl acetate and hexanes to obtain the title compound as solid (540 mg, 32%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed
  3. customCondensed mass
  4. washwashed with aq. sodium bicarbonate solution
  5. customOrganic layer was dried
  6. custom(Na2SO4), condensed
  7. customthe residue was chromatographed

Sources & evidence

ORD record
ord-4ee862ca084142f6b98e984c6c972955
Source dataset
uspto-grants-2008_01
Patent number
US07314889B2

Reaction notes

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