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4-Methoxy-alpha-toluenethiol → 2,5-Dichloro-1-methoxy-3-((4-methoxybenzyl)sulfanyl)benzene

HRID 591426
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HRID 591426 반응식
CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.Br[C:53]1[CH:58]=[C:57]([Cl:59])[CH:56]=[C:55]([O:60][CH3:61])[C:54]=1[Cl:62].[CH3:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([CH2:71][SH:72])=[CH:67][CH:66]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[Cl:62][C:54]1[C:53]([S:72][CH2:71][C:68]2[CH:69]=[CH:70][C:65]([O:64][CH3:63])=[CH:66][CH:67]=2)=[CH:58][C:57]([Cl:59])=[CH:56][C:55]=1[O:60][CH3:61]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 804074-Methoxy-alpha-toluenethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 577991361-Bromo-2,5-dichloro-3-methoxybenzene

생성물 1

HCID 897678422,5-Dichloro-1-methoxy-3-((4-methoxybenzyl)sulfanyl)benzene

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 962Water용매
HCID 1140Toluene용매

실험 절차

To a mixture of DIPEA (5.77 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.488 g), 1-bromo-2,5-dichloro-3-methoxybenzene (4.32 g) and (4-methoxyphenyl)methanethiol (2.47 mL) and toluene (100 mL) was added tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.773 g) at room temperature. The mixture was refluxed for 5 h. After cooling, water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (5.66 g).

후처리

  1. temperatureThe mixture was refluxed for 5 h
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-e91466d0646d48a0bc5cbfed8a475e07
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238639B2

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