1,2-Dibromoethane → 1-(2-bromoethoxy)-2-chloro-4-nitrobenzene

HRID 1820854Notes

Reaction equation

HRID 1820854 reaction equation
[Br:1][CH2:2][CH2:3]Br.C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21]>CN(C=O)C.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][O:21][C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[Cl:11]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12074Nitrofungin

Product 1

HCID 3099731-(2-bromoethoxy)-2-chloro-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

36.6 mL (416 mmol) of 1,2-dibromoethane is dissolved in 200 mL of DMF and 11.5 g (83.3 mmol) of potassium carbonate is added. 7.20 g (41.6 mmol) of 2-chloro-4-nitrophenol in 40 mL of DMF is slowly added dropwise to this mixture. The mixture is stirred for 3 hours at ambient temperature. The solvent is eliminated, the residue is taken up in ethyl acetate and washed with saturated saline solution. The organic phase is dried over sodium sulfate. The solvent is eliminated and the residue is purified through a silica gel column with a gradient of petroleum ether/ethyl acetate (4:1 to 9:1). Yield: 7.9 g (68% of theory); Rf value: 0.55 (silica gel, petroleum ether/ethyl acetate=3:1); C8H7BrClNO3.

Workup

  1. washwashed with saturated saline solution
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe residue is purified through a silica gel column with a gradient of petroleum ether/ethyl acetate (4:1 to 9:1)

Sources & evidence

ORD record
ord-2e2fc764281b4f2db81c52b925c561bf
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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