1-Bromo-2-Chloroethane → 1-Chloro-2-[(2-chloroethyl)oxy]-4-nitrobenzene

HRID 491608Notes

Reaction equation

HRID 491608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14][Cl:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:13][CH2:14][Cl:15]

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 177561821-Chloro-2-[(2-chloroethyl)oxy]-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-5-nitrophenol (4 g, 23 mmol), 1-bromo-2-chloroethane (9 mL, 115 mmol), and K2CO3 (8 g, 58 mmol) in DMF (50 mL) was heated at 80° C. for 18 h. The mixture was diluted with water and extracted several times with EtOAc. The combined organic layers were washed with 1N NaOH (aq) and concentrated in vacuo to yield the title compound and a bromo adduct contaminant.

Workup

  1. extractionextracted several times with EtOAc
  2. washThe combined organic layers were washed with 1N NaOH (aq)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-116b6bf81d2f4fffbc832b106ce0266e
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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