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

HRID 2240045Notes

Reaction equation

HRID 2240045 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[Cl:11][CH2:12][CH2:13][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 69472-NitrophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 43624871-(2-chloroethoxy)-2-nitrobenzeneYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ortho-nitrophenol (5.0 g, 35.8 mmoles) and 2-chloroethanol (9.5 ml, 143 mmoles) in THF (50 mL), in a round bottom flask, under nitrogen, was stirred at room temperature. Triphenylphosphine (14 g, 53.7 mmoles) was added, followed by diethylazodicarboxylate dropwise (8.5 mL, 53.7 mmoles). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, extracted with EtOAc, washed with water (1×), brine (1×), dried (Na2SO4), and concentrated under vacuum. The crude product was purified by flash chromatography using as eluent 40% EtOAc/hexane to give the title compound as an off-white solid (5.6 g, 28 mmoles).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with EtOAc
  3. washwashed with water (1×), brine (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f8f461c0ce404a0abdba072812021676
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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