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N-Iodosuccinimide → 1,5-Di-tert-butyl-3-iodo-2-(2,2,2-trifluoro-ethoxy)-benzene

HRID 1394661
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HRID 1394661 반응식
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18])([CH3:4])([CH3:3])[CH3:2].[I:21]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[CH:8]=[C:7]([I:21])[C:6]=1[O:15][CH2:16][C:17]([F:18])([F:19])[F:20])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 3

HCID 120273N-IodosuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 179527612,4-Di-tert-butyl-1-(2,2,2-trifluoro-ethoxy)-benzene

생성물 1

HCID 179527931,5-Di-tert-butyl-3-iodo-2-(2,2,2-trifluoro-ethoxy)-benzene수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
38 °C

실험 절차

2,4-Di-tert-butyl-1-(2,2,2-trifluoro-ethoxy)-benzene (5.06 g, 17.5 mmol), N-iodosuccinimide (4.74 g, 21 mmol) and p-toluenesulfonic acid monohydrate (1.33 g, 7 mmol) were combined in dichloromethane (50 mL) and heated at 38° C. for 19 h. The reaction was washed with 10% Na2S2O3 solution (2×40 mL). The aqueous was backwashed with dichloromethane (70 mL) and then the combined organic portions washed with water (75 mL) and the combined organic portions washed with water (100 mL), dried (MgSO4), filtered and evaporated in vacuo to provide a yellow oil (6.96 g). The material was purified by flash chromatography using hexane to give 5.85 g (81%) of a light pink oil. 1HNMR (250 MHz, CDCl3): δ 7.67 (d, 1H, J=2.4), 7.37 (d, 1H, J=2.4), 4.45 (q, 2H, J=8.2), 1.40 (s, 9H), 1.30 (s, 9H).

후처리

  1. washThe reaction was washed with 10% Na2S2O3 solution (2×40 mL)
  2. washthe combined organic portions washed with water (75 mL)
  3. washthe combined organic portions washed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a67829a59f6a45209c9af4f9fa52c115
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07348359B2

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