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

HRID 883029Notes

Reaction equation

HRID 883029 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-151ed5f83c3b44b0a3e3faf00259351f
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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