Sodium Iodide → HCID 59259087, compound

HRID 641816Notes

Reaction equation

HRID 641816 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[I-].[Na+].[CH2:15](Br)[C:16]#[CH:17].C(N(C(C)C)C(C)C)C>CC(C)=O>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:17][C:16]#[CH:15])=[CH:9][C:6]=1[CH:7]=[O:8])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7842Propargyl bromideHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 59259087HCID 59259087, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g (150 mmol) 5-hydroxy-2-nitro-benzaldehyde, 44.9 g (299 mmol) sodium iodide, 44.5 g propargyl bromide (80% in toluene), 42 ml N-ethyl-diisopropy-lamine and 400 ml acetone is stirred at rt for 6 d. The reaction mixture is filtered, concentrated, taken up in 1M aqueous hydrochloric acid and extracted with ethyl acetate to yield 2-nitro-5-propargyloxy-benzaldehyde.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-0e173763bb8344d5b735e654e0873d13
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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