Dimethylformamide → 2,5-Difluoro-4-methoxybenzaldehyde

HRID 922272

반응식

HRID 922272 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[F:11].C([Li])CCC.CN([CH:20]=[O:21])C>C1COCC1>[F:11][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[C:6]([F:8])=[CH:7][C:2]=1[CH:20]=[O:21]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 27249834-Bromo-2,5-difluoroanisoleHCID 178418339Butyllithium

생성물 1

HCID 38569382,5-Difluoro-4-methoxybenzaldehyde수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a 250 mL three RB flask fitted with magnetic stirrer was charged 1-Bromo-2,5-difluoro-4-methoxybenzene (1.0 g, 4.5 mmol) in 10 mL of THF, cooled −78° C. To the stirred solvent was added n-butyl lithium (3.09 mL, 1.6M solution, 4.95 mmol) drop wise and stirred at same temperature, was added DMF (0.375 g, 5.13 mmol), once the temperature to reached room temperature and stirred about 16 h. Then reaction mixture was quenched with ice-cold water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4. The removal of solvent under reduced pressure to obtain liquid product (0.77 g, yield: 100.0%).

후처리

  1. customto reached room temperature
  2. stirringstirred about 16 h
  3. customThen reaction mixture
  4. customwas quenched with ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe removal of solvent under reduced pressure

출처 및 근거

ORD 기록
ord-7cfca20889a0403f907ed93675420ff1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278915B2

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