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

HRID 591426
ノート
印刷プレビュー

反応式

HRID 591426 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e91466d0646d48a0bc5cbfed8a475e07
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238639B2

反応ノート

読み込み中…

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