4-Nitrophenol → 1-(2-(4-Nitrophenoxy)ethyl)biphenyl

HRID 1295514Notes

Reaction equation

HRID 1295514 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2](CCO)=[CH:3][CH:4]=[CH:5][CH:6]=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:10]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=[CH:12][CH:13]=[CH:14][CH2:15]2)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22052021[1,1'-Biphenyl]-2-ethanol

Product 1

HCID 692671701-(2-(4-Nitrophenoxy)ethyl)biphenylYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-biphenyl ethanol (1 g, 5 mmol), 4-nitrophenol (834 mg, 6 mmol), and triphenylphosphine (1.59 g, 6 mmol) was dissolved in 20 mL dichloromethane. The solution was chilled in an ice-water bath prior to the addition of diethylazodicarboxylate (949 μl, 6 mmol). The reaction was then stirred overnight, and the ice-water bath slowly warmed to room temperature. Crude product was purified by flash chromatography to yield 640 mg crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 8.1 (d), 7.6 (m), 7.47–7.41 (m), 7.34 (m), 7.17 (m), 4.39 (t, 2H), 3.13 (t, 2H).

Workup

  1. temperatureThe solution was chilled in an ice-water bath
  2. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-363ea620f0de4b73ab9fc9e3b56d177c
Source dataset
uspto-grants-2007_07
Patent number
US07241812B2

Reaction notes

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