Hydrochloric Acid → 3-(4-Bromo-2,5-difluorophenyl)acrylic acid

HRID 533942

반응식

HRID 533942 반응식
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1(C)[O:18]C(=O)CC(=O)[O:14]1.Cl>C(N(CC)CC)C>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[CH:12][C:13]([OH:18])=[O:14])=[C:4]([F:11])[CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 224890814-Bromo-2,5-difluorobenzaldehyde

생성물 1

HCID 867151273-(4-Bromo-2,5-difluorophenyl)acrylic acid

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
95 °C

실험 절차

To a solution of 4-bromo-2,5-difluorobenzaldehyde (15.0 g) in triethylamine formiate (80 mL) at room temperature was added 2,2-dimethyl-1,3-dioxane-4,6-dione (9.77 g). After being stirred for 1 h, the mixture was heated at 95° C. with stirring for 15 hours. After cooling down, ice water was added. The mixture was adjusted to pH ˜1 with HCl (6 M) and then extracted with ethyl acetate (200 mL×3). The organic phase was washed with brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography eluting with DCM/petroleum ether (7:1) to give the subtitle compound as a white solid. MS ESI+: m/z=263 [M+H]+.

후처리

  1. stirringwith stirring for 15 hours
  2. temperatureAfter cooling down
  3. extractionextracted with ethyl acetate (200 mL×3)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with DCM/petroleum ether (7:1)

출처 및 근거

ORD 기록
ord-1bc5e5f3c76f442fbf793ad34471c903
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853412B2

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