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

HRID 1927760노트

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HRID 1927760 반응식
[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

참가 물질

6

반응물 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 574343473-Cyclopropyl-4-fluorobenzaldehyde수율 49.5%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 178418851HCID 178418851, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-ca4eb11cdd5242c3aeed938e9954eb2c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183289B2

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