Water → 2-Cyclopropyl-7-iodo-5-nitrobenzofuran

HRID 575840Notes

Reaction equation

HRID 575840 reaction equation
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([I:11])[C:3]=1[OH:12].[C:13]([CH:15]1[CH2:17][CH2:16]1)#[CH:14].O>N1C=CC=CC=1>[CH:15]1([C:13]2[O:12][C:3]3[C:4]([I:11])=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[CH:14]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 93702,6-Diiodo-4-nitrophenolHCID 138823Cyclopropylacetylene

Product 1

HCID 1180218282-Cyclopropyl-7-iodo-5-nitrobenzofuranYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2,6-diiodo-4-nitrophenol (10 g, 25.6 mmol), ethynylcyclopropane (1.9 g, 28.8 mmol) and Cu2O (1.9 mg, 13.2 mmol) in 100 mL of dry pyridine was refluxed for 2 h. The reaction mixture was poured into 1 L of water and stirred for 10 min. The resulting mixture was filtered. The cake was purified by column chromatography on silica gel eluting with EtOAc/PE (0-20%) to give the title compound (6.6 g, 78% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 8.47 (d, J=2.4 Hz, 1H), 8.32 (d, J=2.4 Hz, 1H), 6.58 (s, 1H), 2.13-2.07 (m, 1H), 1.14-1.04 (m, 4H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customThe cake was purified by column chromatography on silica gel eluting with EtOAc/PE (0-20%)

Sources & evidence

ORD record
ord-4b2f26ebe7c04741a0075a3e848b80ba
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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