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

HRID 511216ノート

反応式

HRID 511216 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 218979121-(Dimethyl-phosphinoyl)-4-nitro-benzene収率 36.3%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-888e2891d838492ab0fee53c43e5e966
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

反応ノート

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