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

HRID 2078837Notes

Reaction equation

HRID 2078837 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-1cf4794d4287474796075a712f272264
Source dataset
uspto-grants-2011_04
Patent number
US07928248B2

Reaction notes

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