Dimethyl Sulfoxide → 2-Fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid

HRID 883029ノート

反応式

HRID 883029 の反応式
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:10][C:11]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[F:10][C:11]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][N:9]=2)=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 27744802-Fluoro-5-hydroxybenzoic acid

生成物 1

HCID 866237872-Fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To 2-chloronicotinaldehyde (381 mg, 2.69 mmol), 2-fluoro-5-hydroxybenzoic acid (300 mg, 1.92 mmol) and cesium carbonate (1.25 g, 3.84 mmol) was added DMSO (2.5 mL). The mixture was heated to 80° C. in a sealed tube for 3 hours. The cooled reaction was diluted with water and extracted with EtOAc. The aqueous layer was acidified with TFA (pH˜3) and extracted with EtOAc. This layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was washed with Et2O dried to yield 2-fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid as an off-white solid. MS m/z=262 [M+1]+. Calc'd for C13H8FNO4: 261.21.

後処理

  1. customThe cooled reaction
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThis layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe residue was washed with Et2O
  8. customdried

出典と根拠

ORDレコード
ord-151ed5f83c3b44b0a3e3faf00259351f
出典データセット
uspto-grants-2012_08
特許番号
US08236823B2

反応ノート

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