6-Bromo-2-fluoro-3-methoxybenzaldehyde → 2-Fluoro-3-methoxy-6-vinylbenzaldehyde

HRID 222314노트

반응식

HRID 222314 반응식
Br[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.[CH:13]([B-](F)(F)F)=[CH2:14].[K+]>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:10][C:6]1[C:5]([O:11][CH3:12])=[CH:4][CH:3]=[C:2]([CH:13]=[CH2:14])[C:7]=1[CH:8]=[O:9]

참가 물질

5

반응물 2

HCID 231579156-Bromo-2-fluoro-3-methoxybenzaldehydeHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 577227732-Fluoro-3-methoxy-6-vinylbenzaldehyde

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 10311-Propanol용매

실험 절차

To a stirred solution of 6-bromo-2-fluoro-3-methoxybenzaldehyde (13 g, 56 mmol) in nPrOH (200 mL) were added potassium vinyltrifluoroborate (7.9 g, 59 mmol), PdCl2(dppf) (0.91 g, 1.1 mmol), and TEA (7.8 mL, 56 mmol). The reaction mixture was purged with N2 for 10 min, heated to reflux for 3 h, cooled to room temperature, treated with water, and concentrated. The residue was extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 10.53 (s, 1H); 7.43 (dd, 1H); 7.31 (d, 1H); 7.16 (t, 1H); 5.60 (d, 1H); 5.36 (d, 1H); 3.95 (s, 3H).

후처리

  1. customThe reaction mixture was purged with N2 for 10 min
  2. temperatureheated
  3. temperatureto reflux for 3 h
  4. additiontreated with water
  5. concentrationconcentrated
  6. extractionThe residue was extracted with EtOAc (×3)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-bd8e3e39fc5340a6bf66c7f53c006236
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207186B2

반응 노트

불러오는 중…