N-bromobutanimide → HCID 23157338、化合物

HRID 2110860ノート

反応式

HRID 2110860 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:16][CH2:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 23157412Methyl 3-isopropoxy-4-methylbenzoate

生成物 1

HCID 23157338HCID 23157338、化合物収率 64.6%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 3-isopropoxy-4-methylbenzoate (1.0 g, 4.8 mmol) in ethyl acetate (20 mL) were added N-bromosuccinimide (0.92 g, 5.19 mmol) and 2,2′-azobis(isobutyronitrile) (3 mg), and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.89 g, yield 64%) as a colorless oil. MS (ESI+): 287 (M+H), 289.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-8d3f1d5bad4d4079bd133a38260a098a
出典データセット
uspto-grants-2009_04
特許番号
US07517910B2

反応ノート

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