2-Nitrophenol → 1-(2-chloroethoxy)-2-nitrobenzene

HRID 1669651Notes

Reaction equation

HRID 1669651 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH2:12][CH2:13][Cl:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:12][CH2:13][Cl:14])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium Carbonate

Product 1

HCID 43624871-(2-chloroethoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-nitrophenol (50.0 g, 0.36 mol), 1-bromo-2-chloroethane (45 mL, 0.54 mol), and K2CO3 (100.0 g, 0.72 mol) in DMF (200 mL) was stirred at 90° C. for 2 h, cooled to room temperature, poured into ice-water, filtered, washed with H2O and dried to give Compound 7, 70.3 g (96%) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-48a3c9d7769b4e96b07c47fdfed2a858
Source dataset
uspto-grants-2011_08
Patent number
US07989617B2

Reaction notes

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