Ethyl bromoacetate → 2-((8-(Trifluoromethyl)quinolin-4-yl)oxy)acetic acid

HRID 1690238Notes

Reaction equation

HRID 1690238 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[Na+]>CS(C)=O>[F:14][C:12]([F:15])([F:13])[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:1][CH2:23][C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 1785164428-(Trifluoromethyl)quinolin-4-ol

Product 1

HCID 534209752-((8-(Trifluoromethyl)quinolin-4-yl)oxy)acetic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Hydroxy-8-trifluoromethylquinoline (0.50 g, 2.35 mmol) was dissolved in DMSO (2 mL). Potassium carbonate was added (0.32 g, 2.35 mmol) and the mixture was stirred vigorously for 2 h. Ethyl bromoacetate (0.32 mL, 1.2 equiv) was added dropwise and heat was applied at 50° C. for 6 h. At 50° C., 2N NaOH (2 mL) was added and stirring continued for 4 h. The mixture was cooled and quenched with water (4 mL). Glacial acetic acid (1.4 mL) was added to ˜pH 4 resulting in precipitation of product. After stirring the suspension for 6 h, the solid was collected by vacuum filtration, rinsed with water, and dried in a vacuum dessicator over CaCl. The yield of white solid was 0.56 g (87%). 1H-NMR (DMSO-d6) 5.04 (s, 2H), 7.11 (d, J=5.2 Hz, 1H), 7.69 (t, J=8.0 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H), 8.47 (d, J=8.0 Hz, 1H), 8.83 (d, J=5.2 Hz, 1H), 13.3 (br s, 1H); LC/MS (10-99%) M/Z: M+1 obs=333.5; tR=2.63 min.

Workup

  1. temperatureheat
  2. waitwas applied at 50° C. for 6 h
  3. stirringstirring
  4. waitcontinued for 4 h
  5. temperatureThe mixture was cooled
  6. customquenched with water (4 mL)
  7. additionGlacial acetic acid (1.4 mL) was added to ˜pH 4
  8. customresulting in precipitation of product
  9. stirringAfter stirring the suspension for 6 h
  10. filtrationthe solid was collected by vacuum filtration
  11. washrinsed with water
  12. dry with materialdried in a vacuum dessicator over CaCl

Sources & evidence

ORD record
ord-88139d87ee1e4601b733de305d3ddc50
Source dataset
uspto-grants-2012_04
Patent number
US08153655B2

Reaction notes

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