Sodium Iodide → 2-Iodo-3',4',5'-tribenzyloxyacetophenone

HRID 1894919Notes

Reaction equation

HRID 1894919 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4].[I-:35].[Na+]>C(#N)C>[I:35][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 576727852-Bromo-3',4',5'-tribenzyloxyacetophenone

Product 1

HCID 576727822-Iodo-3',4',5'-tribenzyloxyacetophenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-3′,4′,5′-tribenzyloxyacetophenone (5.17 g, 10.0 mmol) (11) and sodium iodide (2.25 g, 15 mmol) were dissolved in dry acetonitrile (50 mL) and stirred at room temperature overnight. The solution was filtered and acetonitrile removed under vacuum. Water (30 mL) was added and the solution was extracted with diethyl ether (4×25 mL). The organic phase was dried (MgSO4) and the solvents removed in vacuo. Recrystallisation from methylcyclohexane afforded the titled compound as yellow crystals, m.p. 110-112° C. Yield 3.6 g (64%). 1H NMR (300 MHz, CDCl3): δ=4.21 (2H, s), 5.15 (6H, s), 7.22-7.48 (17H, m); 13C NMR (75 MHz): δ=1.0, 71.3, 75.1, 109.0, 127.4, 127.9, 128.0, 128.1, 128.3, 128.4, 128.5, 136.3, 137.1, 143.4, 152.6, 191.5.

Workup

  1. filtrationThe solution was filtered
  2. customacetonitrile removed under vacuum
  3. additionWater (30 mL) was added
  4. extractionthe solution was extracted with diethyl ether (4×25 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customRecrystallisation from methylcyclohexane

Sources & evidence

ORD record
ord-5c7db2ee15b54cb1ae1caf06d1e7e641
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

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