3-Chloro-2,6-difluorobenzaldehyde → 1-(3-Chloro-2,6-difluorophenyl)prop-2-en-1-ol

HRID 1396306노트

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HRID 1396306 반응식
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH:12]([Mg]Br)=[CH2:13]>C1COCC1>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:5]([OH:6])[CH:12]=[CH2:13])[C:7]([F:10])=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 867102171-(3-Chloro-2,6-difluorophenyl)prop-2-en-1-ol수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

3-Chloro-2,6-difluorobenzaldehyde (1.0 g, 5.66 mmol) was dissolved in THF (28.3 mL) under an atmosphere of argon, and the solution was cooled to −78° C. To the cold solution was then added vinyl magnesium bromide, 1.0 M in THF (8.50 mL, 8.50 mmol) dropwise over 10-15 min. Stirring was continued at −78° C. for 1 h. The reaction was warmed to rt, then cooled to 0° C. and carefully quenched with saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The organic extracts were combined and washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated to yield the desired product as a light yellow oil (1.19 g, 98%). MS (ESI) m/z: 187.0 (M−H2O)+. 1H NMR (500 MHz, CDCl3) δ 7.36-7.30 (m, 1H), 6.88 (td, J=9.2, 1.9 Hz, 1H), 6.21 (dddt, J=17.1, 10.3, 5.8, 1.1 Hz, 1H), 5.59 (dd, J=7.4, 6.6 Hz, 1H), 5.33 (dd, J=17.1, 0.8 Hz, 1H), 5.26 (dt, J=10.3, 1.2 Hz, 1H), 2.35 (dt, J=8.5, 1.8 Hz, 1H).

후처리

  1. temperatureThe reaction was warmed to rt
  2. temperaturecooled to 0° C.
  3. customcarefully quenched with saturated NH4Cl solution
  4. additionThe mixture was diluted with water
  5. extractionextracted with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-fec8f0dd0dd14e5db9548b3cbdf2817d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901115B2

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