Hydrochloric Acid → 2-Chloro-3-fluoro-4-methoxybenzaldehyde

HRID 1945104노트

반응식

HRID 1945104 반응식
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN([CH:19]=[O:20])C.Cl>C1COCC1.CCCCCC>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][C:7]=1[CH:19]=[O:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 27735843-Chloro-2-fluoroanisoleHCID 178418339Butyllithium

생성물 1

HCID 538390722-Chloro-3-fluoro-4-methoxybenzaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF are cooled to −70° C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After one hour at −70° 3.93 ml DMF in 7 ml THF are added at −70° C. and the mixture is stirred another hour at −70° C. 15 ml of a 1 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); δ=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

후처리

  1. temperaturethe reaction is warmed to ambient temperature over 18 hours
  2. customThe reaction mixture is partitioned between diethyl ether and water
  3. extractionThe aqueous phase is extracted with diethyl ether
  4. washthe combined organic phases are washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe crude product is purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-6798d3e44494468587952719ff4efde8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394958B2

반응 노트

불러오는 중…