Dimethyl Sulfide → Methyl 2-fluoro-6-formylbenzoate

HRID 1476809노트

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HRID 1476809 반응식
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=C)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O:14]=[O+][O-].CSC>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[O:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 90387241Methyl 2-fluoro-6-vinylbenzoate

생성물 1

HCID 87166864Methyl 2-fluoro-6-formylbenzoate수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Into a solution of methyl 2-fluoro-6-vinylbenzoate (31 g, 0.172 mol) in dry dichloromethane (300 mL) was bubbled O3 at −78° C. over a 30 minute period. Next, nitrogen gas was bubbled into the solution until it turned colorless. Dimethylsulfane (84.13 g, 1.36 mol) was added dropwise to the solution, which was subsequently warmed to RT and stirred for 2 hours. The mixture was then washed with water (30 mL) and extracted with DCM (3×300 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by column chromatography eluting with a gradient of EtOAc (10-100%) and PE to give the title compound (21 g, 67%). 1H NMR (400 MHz, CDCl3) δ ppm 10.01 (s, 1H), 7.65-7.63 (d, J=7.6 Hz, 1H), 7.56-7.53 (dd, J1=5.2 Hz, J2=8.0 Hz, 1H), 7.35-7.30 (t, J=8.4 Hz, 1H), 3.94 (s, 3H).

후처리

  1. customNext, nitrogen gas was bubbled into the solution until it
  2. washThe mixture was then washed with water (30 mL)
  3. extractionextracted with DCM (3×300 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with a gradient of EtOAc (10-100%) and PE

출처 및 근거

ORD 기록
ord-766c4db37b984116a7c7ede596bc53b6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09402841B2

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