Hydrochloric Acid → Tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoate

HRID 69111

反応式

HRID 69111 の反応式
[Cl-].[Mg+2].[Cl-].[O:4]=[C:5]([CH3:14])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1.Cl>O1CCCC1.C(OCC)(=O)C.O.N1C=CC=CC=1>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([CH:6]([C:5](=[O:4])[CH3:14])[C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])=[O:21])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 15538Tert-butyl acetoacetateHCID 5360315Magnesium ChlorideHCID 189198804-Bromo-2-nitrobenzoyl chloride

生成物 1

HCID 86694315Tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoate収率 64%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-8 °C

実験手順

Under a nitrogen atmosphere, to a suspension of 2.28 g of magnesium chloride in 50 mL of tetrahydrofuran was added 3.80 g of tert-butyl 3-oxobutanoate at room temperature. The mixture was cooled to −8° C., and 3.9 mL of pyridine was added thereto, followed by stirring at the same temperature for 30 minutes, warming to room temperature, and further stirring for 30 minutes. The mixture was cooled to −8° C., and a solution of 5.3 g of 4-bromo-2-nitrobenzoyl chloride in 20 mL of tetrahydrofuran was added thereto, followed by stirring at the same temperature for 1 hour, warming to room temperature, and further stirring for 1.5 hours. The mixture was poured into a mixture of water and ethyl acetate, and adjusted to pH 3 with concentrated hydrochloric acid. The aqueous layer was separated, and then the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4.95 g of tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3 -oxobutanoate.

後処理

  1. temperaturewarming to room temperature
  2. stirringfurther stirring for 30 minutes
  3. temperatureThe mixture was cooled to −8° C.
  4. stirringby stirring at the same temperature for 1 hour
  5. temperaturewarming to room temperature
  6. stirringfurther stirring for 1.5 hours
  7. customThe aqueous layer was separated
  8. washthe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-2785f0f145504683ba851c929693a5f8
出典データセット
uspto-grants-2014_09
特許番号
US08822448B2

関連ノート

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