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

HRID 1894919노트

반응식

HRID 1894919 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c7db2ee15b54cb1ae1caf06d1e7e641
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513395B2

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