Dimethylformamide → 6-Bromo-2-fluoro-3-propylbenzaldehyde

HRID 718482노트

반응식

HRID 718482 반응식
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[C:12]([F:19])[CH:11]=1.CN([CH:23]=[O:24])C>C1COCC1>[Br:9][C:10]1[C:11]([CH:23]=[O:24])=[C:12]([F:19])[C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 215898314-Bromo-2-fluoro-1-propylbenzene

생성물 1

HCID 866960636-Bromo-2-fluoro-3-propylbenzaldehyde수율 39.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

Under a nitrogen atmosphere, LDA (50.7 mL, 56.25 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (100 mL) solution of 4-bromo-2-fluoro-1-propylbenzene (50) (11.1 g, 51.13 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (6.15 g, 76.70 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 60 mL of toluene 3 times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over magnesium sulfate and a solvent was distilled off by evaporator. The residue was purified by silica gel column chromatography, and thus 6-bromo-2-fluoro-3-propylbenzaldehyde (51) (5.0 g, yield 36%) was obtained.

후처리

  1. customwas returned to room temperature
  2. customquenched with 100 mL of 1N hydrochloric acid aqueous solution
  3. extractionextracted with 60 mL of toluene 3 times
  4. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationa solvent was distilled off by evaporator
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0f1cdce2f3b84a528713ea345a888ec4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193908B2

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