3-Bromo-4-fluorobenzaldehyde → 3-Cyclopropyl-4-fluorobenzaldehyde

HRID 453528ノート

反応式

HRID 453528 の反応式
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Br[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=[O:11]>C1COCC1.[Cl-].[Zn+2].[Cl-].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[F:15])[CH:10]=[O:11])[CH2:3][CH2:2]1

参加物

6

反応物 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418630HCID 178418630、化合物

生成物 1

HCID 574343473-Cyclopropyl-4-fluorobenzaldehyde収率 49.5%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 178418851HCID 178418851、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A flask was charged with cyclopropyl magnesium bromide (29.6 ml, 14.8 mmol) and placed under nitrogen. Zinc chloride (14.8 ml, 14.8 mmol) was added and the reaction was stirred for 20 minutes. 3-Bromo-4-fluorobenzaldehyde (1.0 g, 4.93 mmol) and bis(tri-t-butylphosphine)palladium (0) (0.126 g, 0.246 mmol) were diluted in 600 μL of THF and added to the reaction mixture. After stirring for 4 hours, the reaction was heated to 50° C. and stirred overnight. The reaction was cooled and quenched with saturated NH4Cl and extracted with DCM. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M cartridge eluting with hexanes:ethyl acetate (4:1) to yield 3-cyclopropyl-4-fluorobenzaldehyde (400 mg, 49.5% yield)

後処理

  1. additionadded to the reaction mixture
  2. stirringAfter stirring for 4 hours
  3. stirringstirred overnight
  4. temperatureThe reaction was cooled
  5. customquenched with saturated NH4Cl
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified
  11. washeluting with hexanes:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-226347ba743f4da583217f5678573b73
出典データセット
uspto-grants-2013_07
特許番号
US08492437B2

反応ノート

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