Sodium Iodide → HCID 86652902, compound

HRID 1260138Notes

Reaction equation

HRID 1260138 reaction equation
[I-:1].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([CH2:17][OH:18])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15]Br)[C:4]#[CH:5]>CC(C)=O>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([CH2:17][OH:18])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][I:1])[C:4]#[CH:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86652901HCID 86652901, compound

Product 1

HCID 86652902HCID 86652902, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Sodium iodide (10 g, 70 mmol, 4 equiv) was added in one portion to the stirred solution of 10 (5 g, 18 mmol, 1 equiv) in acetone (40 mL). The mixture was heated to 50° C. under nitrogen overnight. Upon reaction completion, the solvent was removed under vacuum. The resulting solid was dissolved in CH2Cl2 (200 mL) and washed subsequently with sodium thiosulfate solution (2×200 mL), water (200 mL) and brine (200 mL). The organic layer was dried over MgSO4, filtered and solvent was removed under vacuum to afford product as a white solid (5.71 g, yield: 98%). 1H NMR δ=7.09 (d, J=1.8, 1H), 6.96 (dd, J1=1.8, J2=8, 1H), 6.91 (d, J=8, 1H), 4.78 (d, J=2.3, 2H, —OCH2C≡CH), 4.63 (d, J=5.8, 2H, —CH2OH), 4.30 (t, J=6.6, 2H, —OCH2CH2I), 3.45 (t, J=6.6, 2H, —OCH2CH2I), 2.51 (t, J=2.3, 1H, —C≡CH), 1.68 (t, J=5.8, 1H, —CH2OH). 13C NMR δ=147.80, 145.50, 135.14, 121.22, 115.33, 114.86, 78.74 (—C≡CH), 76.09 (—C≡CH), 70.44 (—CH2OH), 65.21 (—OCH2CH2I), 57.38 (—OCH2C≡CH), 1.32 (—OCH2CH2I). HRMS calculated for C12H11BrO3 (M−OH+), 267.0021; found, 267.0008.

Workup

  1. customUpon reaction completion
  2. customthe solvent was removed under vacuum
  3. dissolutionThe resulting solid was dissolved in CH2Cl2 (200 mL)
  4. washwashed subsequently with sodium thiosulfate solution (2×200 mL), water (200 mL) and brine (200 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customsolvent was removed under vacuum

Sources & evidence

ORD record
ord-c1662c9afbd1462ca41995188022d62e
Source dataset
uspto-grants-2013_06
Patent number
US08470587B2

Reaction notes

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