Bromine → Diethyl 2-bromo-3,4,5-trimethoxyphenylphosphonate

HRID 1384047ノート

反応式

HRID 1384047 の反応式
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[C:10]([O:11][CH3:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]

参加物

5

反応物 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 21185491Diethyl 3,4,5-trimethoxyphenylphosphonate

生成物 1

HCID 21185533Diethyl 2-bromo-3,4,5-trimethoxyphenylphosphonate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of bromine (10 mmol) in 10 mL of acetic acid is added dropwise to a solution of ester 11 (10 mmol) in 10 mL of acetic acid cooled by an ice water bath. After the red color of the resulting mixture is discharged, the mixture is poured into saturated NaHCO3 (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution is apparent. The organic phases are then washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a pale yellow solid.

後処理

  1. temperaturecooled by an ice water bath
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution
  4. washThe organic phases are then washed with brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe mixture is purified by flash chromatography

出典と根拠

ORDレコード
ord-702929a001ca4b3f906d225203390d9a
出典データセット
uspto-grants-2001_07
特許番号
US06258360B1

反応ノート

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