Trimethyl phosphite → (2,4-Dimethyl-phenyl)-phosphonic acid dimethyl ester

HRID 217263

반응식

HRID 217263 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[P:10]([O:15]C)([O:13][CH3:14])[O:11][CH3:12]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:11][P:10]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9])(=[O:15])[O:13][CH3:14]

참가 물질

5

반응물 2

HCID 8472Trimethyl phosphiteHCID 778854-Iodo-m-xylene

생성물 1

HCID 13836142(2,4-Dimethyl-phenyl)-phosphonic acid dimethyl ester수율 95%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

4-Iodo-m-xylene (8.62 mmol), trimethyl phosphite (12.07 mmol) and palladium acetate (0.86 mmol) were mixed together in acetonitrile (12 ml), in a microwave tube. The vessel was sealed and placed in a microwave to react at 160° C., for 45 minutes. After cooling to room temperature, acetonitrile was removed. The crude material was purified by silica gel chromatography to yield Intermediate I.4 as an oil (95%). Intermediate 1.4 was characterized by the following spectroscopic data: 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.35 (s, 3H), 2.51 (s, 3H), 3.74 (d, J=12.0 Hz, 6H), 7.08-7.09 (m, 2H), 7.75-7.81 (m, 1H); 31P NMR (CDCl3, 162 MHz) δ (ppm) 23.18 (s, 1P); and MS (ESI, EI+) m/z=215 (MH+)

후처리

  1. customThe vessel was sealed
  2. customto react at 160° C., for 45 minutes
  3. customacetonitrile was removed
  4. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-340453ed0be94861bc1cec1be7884551
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193372B2

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