4-Bromoanisole → Bis(4-methoxyphenyl)phenylphosphine oxide

HRID 967678

反応式

HRID 967678 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.Cl[P:12](=[O:20])(Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>BrCCBr.O1CCCC1>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([P:12](=[O:20])([C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:5]=1

参加物

6

反応物 3

HCID 77304-BromoanisoleHCID 69990Phenylphosphonic dichlorideHCID 5462224Magnesium

生成物 1

HCID 4589182Bis(4-methoxyphenyl)phenylphosphine oxide収率 93%

試薬・触媒・溶媒 2

HCID 78391,2-Dibromoethane触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A slurry of magnesium (133.7 g, 5.50 mol), tetrahydrofuran (988 g), and 1,2-dibromoethane (0.1 g, 0.5 mmol) was refluxed for 20 min. under a blanket of nitrogen. 4-Bromoanisole (1002 g, 5.357 mol) was added by drop over 6 h at a rate to maintain 70° C. The reaction mixture was heated for an additional hour. Dichlorophenylphosphine oxide (479.4 g, 2.459 mol) was added by drop to maintain a temperature of 35° C. over 5 h. The reaction mixture was worked up to give bis(4-methoxyphenyl)phenylphosphine oxide (770.8 g, 93% yield) as a viscous amber oil. 31P NMR: (d6-DMSO) δ 30.2 (s).

後処理

  1. temperatureThe reaction mixture was heated for an additional hour
  2. temperatureto maintain a temperature of 35° C. over 5 h

出典と根拠

ORDレコード
ord-7bdb4826e01942ac9a6045b74fe87bf9
出典データセット
uspto-grants-2005_10
特許番号
US06955851B2

関連ノート

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