m-Chloroperbenzoic acid → 5-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

HRID 38983

反応式

HRID 38983 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[C:6]([CH:9]=1)C=O.C1C=C(Cl)C=C([C:22]([O:24]O)=[O:23])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:22]([O:24][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][CH:12]1[CH2:14][O:13]1)=[O:23]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde

生成物 1

HCID 212210275-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 5-bromo-2-(oxiran-2-ylmethoxy)benzaldehyde (12.3 g, 47.7 mmol) in DCM (50 ml) was added m-CPBA (12.8 g, 57.2 mmol). The solution was heated at reflux for 3 h and 30 min and then brought to ambient temperature. Aqueous sodium bicarbonate (saturated) and DCM was added and the phases were separated. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness to give the crude title compound. Crude yield: 12.3 g. MS m/z (rel. intensity, 70 eV) 272 (M+, 7), 244 (50), 189 (95), 188 (bp), 57 (93).

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h and 30 min
  3. custombrought to ambient temperature
  4. customthe phases were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-767b3078aa2d471d93d3027cc3832986
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

関連ノート

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