Hydrochloric Acid → HCID 57894125, compound

HRID 1822304Notes

Reaction equation

HRID 1822304 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2].[Br:24][C:25]1[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:28]=[CH:29][C:30]=1F.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.CCOCC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]([F:21])[CH:17]=[C:18]([O:20][C:30]3[CH:29]=[CH:28][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:26][C:25]=3[Br:24])[CH:19]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1442953-Bromo-4-fluorobenzotrifluorideHCID 57894169HCID 57894169, compound

Product 1

HCID 57894125HCID 57894125, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-[4-(3-fluoro-5-hydroxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.557 g, 1.75 mmol), 3-bromo-4-fluorobenzotrifluoride (0.425 g, 1.75 mmol) and 325 mesh potassium carbonate (0.29 g, 2.10 mmol) in dry DMSO (10 mL) is heated to 100° C. and stirred 2.5 hours under N2. The reaction is cooled and acidified with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 5/1 hexanes/ethyl acetate to afford 0.735 g (78%) of the title compound. 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C2H21O4F4Br 540, found 558 and 560 (M+NH4, 100%).

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customthe solvent is removed in vacuo
  5. customto afford crude product that
  6. customis absorbed on silica gel
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-36dc138a9ffa41e48940ad960fa3d1ad
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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