2-Bromoethanol → 3-(2-bromoethoxy)benzonitrile

HRID 747775Notes

Reaction equation

HRID 747775 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[C:5]([C:7]1[CH:8]=[C:9](O)[CH:10]=[CH:11][CH:12]=1)#[N:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][O:4][C:11]1[CH:12]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:5]#[N:6]

Participants

7

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 177889413-(2-bromoethoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.71 ml (10.0 mmol) of 2-bromoethanol, 1.43 g (12.0 mmol) of 3-cyanophenol and 3.15 g (12.0 mmol) of triphenylphosphine were dissolved in 100 ml of tetrahydrofuran. 5.22 g (12.0 mmol) of diethyl azodicarboxylate (40% solution in toluene) was added to the solution at room temperature, and they were stirred overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained. This product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThis product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-61c0efe79f854a5587d10ba839da6040
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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