Water → 1-(2-bromoethoxy)-2-nitrobenzene

HRID 1629118Notes

Reaction equation

HRID 1629118 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[OH-].[Na+].O.[Br:14][CH2:15][CH2:16]Br>>[Br:14][CH2:15][CH2:16][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 962WaterHCID 69472-NitrophenolHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 3100071-(2-bromoethoxy)-2-nitrobenzeneYield 63%

Conditions

Temperature
107 °C

Procedure

To 2-nitrophenol (25.0 g, 0.180 mol) in sodium hydroxide (14.4 g, 359 mmol) and Water (6.0 mL, 330 mmol) in a 500 mL flask at 107° C. with a reflux condenser was added 1,2-dibromoethane (61.9 mL, 719 mmol), and the flask was heated at 107° C. for three days (FIG. 18). Then, the product was extracted twice with 100 mL DCM, washed with 2M NaOH and brine, dried with sodium sulfate, and concentrated. Silica gel chromatography eluting with hexanes and ethyl acetate provided the bromide 82 in 63% yield. 1H NMR (500 MHz, CDCl3) δ 7.83 (dd, J=8.4, 1.6 Hz, 1H), 7.53 (td, J=8.1, 1.6 Hz, 1H), 7.12-7.01 (m, 2H), 4.45-4.34 (m, 2H), 3.67 (t, J=6.5 Hz, 2H), according to: WO 2002076926

Workup

  1. extractionThen, the product was extracted twice with 100 mL DCM
  2. washwashed with 2M NaOH and brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-b9af9ffff73743b7a6d8d06647b93803
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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