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

HRID 1987141노트

반응식

HRID 1987141 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-42d8d05eba7d410494dbb9a287c1de5c
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550478B2

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