1,2-Dibromoethane → 1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

HRID 1987918Notes

Reaction equation

HRID 1987918 reaction equation
[K].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13].[Br:14][CH2:15][CH2:16]Br.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.C(Cl)Cl>[Br:14][CH2:15][CH2:16][O:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[O:3][CH3:2]

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 767382-Methoxy-4-nitrophenolHCID 5462222Potassium

Product 1

HCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzeneYield 72.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the potassium salt of 2-methoxy-4-nitrophenol (2.07 g, 10.0 mmol), 1,2-dibromoethane (1.72 mL, 20.0 mol), 1 N KOH (50 mL), tetrabutyl ammonium bromide (3.22 g 10.0 mol), and CH2Cl2 was stirred overnight. The reaction was diluted with 300 mL of EtOAc, washed with sat. NH4Cl solution (2×50 mL). The organic layer was dried over Na2SO4 prior to concentration in vacuum to a yellow solid. The solid was then washed with MeOH (2×5 mL) to yield 2.0 g (72%) of the title compound as a white solid. MS (ESI) 276, 278 (M+H)+.

Workup

  1. washwashed with sat. NH4Cl solution (2×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationto concentration in vacuum to a yellow solid
  4. washThe solid was then washed with MeOH (2×5 mL)

Sources & evidence

ORD record
ord-16c3d41e3f9a46bc97fa237344188b93
Source dataset
uspto-grants-2009_06
Patent number
US07553836B2

Reaction notes

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