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

HRID 883029노트

반응식

HRID 883029 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-151ed5f83c3b44b0a3e3faf00259351f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236823B2

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