Methyl 4-bromobenzoate → Methyl 4-[methoxy(phenyl)phosphoryl]benzoate

HRID 1013450

反応式

HRID 1013450 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]1([P:18]([O:21]C)[O:19][CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O>[CH3:20][O:19][P:18]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:21]

参加物

4

反応物 2

HCID 12081Methyl 4-bromobenzoateHCID 76277Dimethyl phenylphosphonite

生成物 1

HCID 57925936Methyl 4-[methoxy(phenyl)phosphoryl]benzoate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

From a related procedure (Helv. Chim. Acta, 2004, 87, 825) a mixture of methyl 4-bromobenzoate (676 mg, 3.14 mmol), anhydrous NiBr2 (34.3 mg, 0.157 mmol), and PhP(OMe)2 (0.500 mL, 3.14 mmol) was added to a pressure vessel and heated to 160° C. (oil bath temperature) for 2 h. The reaction was cooled, diluted with EtOAc and washed with water (3×), brine, dried (MgSO4) and concentrated to afford ˜800 mg of a clear, colorless oil that solidified upon standing. The product was purified by MPLC (15-50% EtOAc in CH2Cl2) to afford the requisite product: MS: cal'd 291 (MH+), exp 291 (MH+).

後処理

  1. additionwas added to a pressure vessel
  2. temperatureThe reaction was cooled
  3. washwashed with water (3×), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford ˜800 mg of a clear, colorless oil that
  7. customThe product was purified by MPLC (15-50% EtOAc in CH2Cl2)
  8. customto afford the requisite product

出典と根拠

ORDレコード
ord-3369c978849642729c86f4c672298b2b
出典データセット
uspto-grants-2011_07
特許番号
US07981874B2

関連ノート

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