Trifluoroacetic acid → HCID 58042402, compound

HRID 2048116Notes

Reaction equation

HRID 2048116 reaction equation
[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:18]=[N:19][C:20]([CH:24]3[CH2:26][CH2:25]3)=[C:21]([Cl:23])[CH:22]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:18]=[N:19][C:20]([CH:24]3[CH2:25][CH2:26]3)=[C:21]([Cl:23])[CH:22]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58042480HCID 58042480, compound

Product 1

HCID 58042402HCID 58042402, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl 5-chloro-4-[(5-chloro-6-cyclopropylpyridin-3-yl)oxy]-2-fluorobenzoate (Preparation 264, 54.0 g, 135.59 mmol) in dichloromethane (270 mL) was added trifluoroacetic acid (30.76 mL, 406.77 mmol). The resulting solution was heated at 45° C. for 24 hours and concentrated under reduced pressure at 45° C. tert Butyl methyl ether (100 mL) was added to the residue and the resulting slurry stirred at room temperature for 2.5 hours, filtered, washed with tert butyl methyl ether (20 mL) and dried to give the title compound as an off-white solid (45.0 g, 97%).

Workup

  1. concentrationconcentrated under reduced pressure at 45° C. tert Butyl methyl ether (100 mL)
  2. additionwas added to the residue
  3. filtrationfiltered
  4. washwashed with tert butyl methyl ether (20 mL)
  5. customdried

Sources & evidence

ORD record
ord-6aa7c4dcabb942ceb29551a63a210785
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

Loading…