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

HRID 1894919ノート

反応式

HRID 1894919 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5c7db2ee15b54cb1ae1caf06d1e7e641
出典データセット
uspto-grants-2013_08
特許番号
US08513395B2

反応ノート

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