2-Iodophenol → 3-(2-(2-Iodophenoxy)ethyl)thiophene

HRID 1949732Notes

Reaction equation

HRID 1949732 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][S:9][CH:10]=1

Participants

5

Reactant 3

HCID 107842-IodophenolHCID 83731Thiophene-3-ethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 640847853-(2-(2-Iodophenoxy)ethyl)thiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-iodophenol (6.7 g, 30.6 mmol), 2-(3-thienyl)ethanol (3.57 g, 27.8 mol) and triphenylphosphene (8.00 g, 30.6 mmol) in THF, was slowly added a solution of DEAD (4.8 ml, 30.6 mmol). Reaction mixture was stirred at room temperature for 3 hours. Purification on silica gave 3-[2-(2-iodo-phenoxy)-ethyl]-thiophene. A mixture of 3-[2-(2-iodo-phenoxy)-ethyl]-thiophene (1.55 g, 4.69 mmol), palladium(II) acetate (105 mg, 0.47 mmol), potassium carbonate (3.2 g, 23.45 mmol), triphenylphosphene (246 mg, 0.94 mmol) and tetraethylammonium chloride (1.3 g, 4.69 mmol) in DMF was microwaved at 100° C. for 1 hour. The reaction was diluted with dichloromethane and filtered through celite. The filtrate was washed with water, dried (MgSO4), and concentrated in-vacuo. Purification on silica gave 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine.

Workup

  1. customReaction mixture
  2. customPurification on silica

Sources & evidence

ORD record
ord-cbd2413b712a44f9971cb621ba41ba13
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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