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

HRID 1396306ノート

反応式

HRID 1396306 の反応式
[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

参加物

4

反応物 2

HCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 178418507HCID 178418507、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fec8f0dd0dd14e5db9548b3cbdf2817d
出典データセット
uspto-grants-2014_12
特許番号
US08901115B2

反応ノート

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