Hydrochloric Acid → Ethyl[4-({3-[3-phenyl-8-(trifluoromethyl)quinolin-yl]phenoxy}methyl)phenyl]acetate

HRID 2104608Notes

Reaction equation

HRID 2104608 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([C:16]=2C2C=C(O)C=CC=2)=[CH:14][CH:13]=[CH:12][C:11]=3[C:24]([F:27])([F:26])[F:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](=[O:31])([O-])[O-].[K+].[K+].[CH2:34]([O:36][C:37](=[O:47])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=1)[CH3:35].Cl>CN(C=O)C>[CH2:34]([O:36][C:37](=[O:47])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][O:31][C:28]2[CH:5]=[CH:6][CH:1]=[C:2]([C:8]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:16][C:15]4[C:10](=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:12]=[CH:13][CH:14]=4)[N:9]=3)[CH:3]=2)=[CH:41][CH:40]=1)[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15712209Ethyl 2-(4-(bromomethyl)phenyl)acetateHCID 665862923-(3-Phenyl-8-trifluoromethyl-quinolin-4-yl)-phenol

Product 1

HCID 131727587Ethyl[4-({3-[3-phenyl-8-(trifluoromethyl)quinolin-yl]phenoxy}methyl)phenyl]acetateYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenol (0.178 g, 0.487 mmol), and potassium carbonate (0.134 g, 0.974 mmol), in DMF at 120° C. is added 4-bromomethylphenylacetic acid ethyl ester (0.334 g, 1.46 mmol), drop wise over 2 h. After an additional 2 h, the cooled reaction is poured into 2N aq HCl and extracted with ethyl acetate. The combined extracts are washed with sat aq NaHCO3, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:9 ethyl acetate:hexanes to afford the title compound as a syrup (0.051 g, 37%). MS m/z 542; HRMS: calcd for C33H26NF3O3+H, 542.19430; found (ESI, [M+H]+), 542.194.

Workup

  1. waitAfter an additional 2 h
  2. customthe cooled reaction
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with sat aq NaHCO3, water, brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe extracts are concentrated
  7. customthe residue is chromatographed with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-a63aeddca4254a6388a9235a4eb163c2
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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