Water → tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

HRID 512039Notes

Reaction equation

HRID 512039 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8].[F:11][C:12]1[CH:24]=[C:23](F)[C:22]([F:26])=[CH:21][C:13]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:23]2[C:22]([F:26])=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[C:12]([F:11])[CH:24]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10868153Tert-butyl 2,4,5-trifluorobenzoateHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoateYield 96.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (5,6-dichloropyridin-3-yl)methanol (275 mg, 1.55 mmol) in DMSO (5 mL) were added tert-butyl 2,4,5-trifluorobenzoate (Preparation 97, 300 mg, 1.30 mmol), and potassium carbonate (535 mg, 3.88 mmol) and the mixture stirred for 18 hours at room temperature under a nitrogen atmosphere. Water (10 mL) was added and the mixture extracted with EtOAc (3×20 mL). The combined organics were washed with water (20 mL) and concentrated in vacuo to yield the title compound (490 mg, 96%).

Workup

  1. extractionthe mixture extracted with EtOAc (3×20 mL)
  2. washThe combined organics were washed with water (20 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c169087eda74b48a0dfa7e99d13ed25
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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