2,5-Dichlorophenol → 2-[4-Chloro-1-(2,5-dichlorophenoxy)butyl]thiophene

HRID 352109Notes

Reaction equation

HRID 352109 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[OH:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[O:6][C:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=1[Cl:19]

Participants

6

Reactant 4

HCID 662,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22715117alpha-(3-Chloropropyl)-2-thiophenemethanol

Product 1

HCID 227151352-[4-Chloro-1-(2,5-dichlorophenoxy)butyl]thiopheneYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-1-thiophen-2-yl-butan-1-ol (2.98 g, 15.6 mmol), 2,5-dichlorophenol (2.55 g, 15.6 mmol) and triphenylphosphine (4.91 g,18.7 mmol) were dissolved in anhydrous tetrahydrofuran (80 ml) and the solution cooled to 0° C. Diethyl azodicarboxylate (3.26 g, 18.7 mmol) was added dropwise and the reaction allowed to warm to room temperature, then stirred for 5 hours. The solvent was removed in vacuo and the residue passed down a flash silica chromatography column, eluting with hexane:ethyl acetate (9:1) to give the title compound as a colourless oil (3.0 g, 57%).

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed in vacuo
  3. washeluting with hexane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-b871a63029524d5eaac091dcb44f35a9
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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