2-Hydroxy-5-methoxybenzaldehyde → 2-Hydroxy-3-iodo-5-methoxy-benzaldehyde

HRID 1835974노트

반응식

HRID 1835974 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(O[I:16](OC(=O)C)([O-])(=O)=O)(=O)C.C([N+](CC)(CC)CC)C>ClCCl>[OH:1][C:2]1[C:9]([I:16])=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

4

반응물 2

HCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 86589546Tetraethylammonium diacetoxyiodate2회

생성물 1

HCID 222215902-Hydroxy-3-iodo-5-methoxy-benzaldehyde수율 11.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-hydroxy-5-methoxy-benzaldehyde (15.97 g, 104.9 mmole) in 375 mL dichloromethane at −15° C. was added tetraethylammonium diacetoxyiodate (48.06 g, 128.1 mmole) over 15 minutes. After stirring overnight, an additional amount of tetraethylammonium diacetoxyiodate (46.93 g, 125.1 mmole) was added over 15 minutes. The reaction was stirred for an additional 12 hours, concentrated, and added to 2N HCl. The mixture was extracted into ethyl acetate and the combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated in vacuo and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 3.47 g (11.9%) of iodide as a yellow solid: Mp=103-105° C.; 1H NMR (DMSO-d6) δ 11.3 (s, 1 H), 9.73 (s, 1 H), 7.60 (d, 1 H, J=3.0 Hz,), 7.07 (d, 1 H, J=3.1 Hz), 3.83 (s, 3 H).

후처리

  1. stirringThe reaction was stirred for an additional 12 hours
  2. concentrationconcentrated
  3. additionadded to 2N HCl
  4. extractionThe mixture was extracted into ethyl acetate
  5. washthe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe organic phases were concentrated in vacuo
  8. customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)

출처 및 근거

ORD 기록
ord-63df1c3db7724a3ab49db6395064846e
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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