Cesium carbonate → 1-(Dimethyl-phosphinoyl)-4-nitro-benzene

HRID 511216

반응식

HRID 511216 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][PH:12](=[O:14])[CH3:13].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:11][P:12](=[O:14])([CH3:13])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 124951-Iodo-4-nitrobenzeneHCID 178503022methylphosphonoylmethane

생성물 1

HCID 218979121-(Dimethyl-phosphinoyl)-4-nitro-benzene수율 36.3%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A degassed suspension of 1-iodo-4-nitrobenzene (90 mg, 0.36 mmol), dimethylphosphane oxide (29.2 mg, 0.38 mmol), bis(dibenzylideneacetone)palladium (3.31 mg, 0.0036 mmol), XantPhos (6.27 mg, 0.0108 mmol), and Cs2CO3 (165 mg, 0.506 mmol) in dry dioxane (0.4 mL) was heated in a sealed tube at 90° C. for 4 h. The cooled mixture was filtered, the filtrate concentrated in vacuo, and the residue chromatographed over silica gel eluting with 5% MeOH in dichloromethane to afford 26 mg of dimethyl(4-nitrophenyl)phosphane oxide (yield: 36%).

후처리

  1. filtrationThe cooled mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe residue chromatographed over silica gel eluting with 5% MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-888e2891d838492ab0fee53c43e5e966
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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