Dimethyl Sulfide → Methyl 2-fluoro-6-formylbenzoate

HRID 1476809ノート

反応式

HRID 1476809 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 87166864Methyl 2-fluoro-6-formylbenzoate収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-766c4db37b984116a7c7ede596bc53b6
出典データセット
uspto-grants-2016_08
特許番号
US09402841B2

反応ノート

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