Hydrochloric Acid → HCID 57894211, compound

HRID 1822338Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[CH:8][C:7]=1[CH3:20].[Br:22][C:23]1[CH:24]=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:27][C:28]=1F.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:28]3[CH:27]=[CH:26][C:25]([C:30]([F:33])([F:32])[F:31])=[CH:24][C:23]=3[Br:22])[CH:14]=2)=[CH:8][C:7]=1[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[4-(3-hydroxy-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (8.18 g, 28.6 mmol), 3-bromo-4-fluorobenzotrifluoride (6.80 g, 28.0 mmol) and 325 mesh potassium carbonate (4.64 g, 33.68 mmol) in dry DMSO (80 mL) is heated to 100° C. and stirred 6 hours under N2. The reaction is cooled and acidified with 1 N HCl. The mixture is diluted with water and extracted with Et2O. 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 15/1 hexanes/ethyl acetate to afford 11.74 g (81%) of the titled compound. Rf=0.76 (9/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C24H20O4F3Br 509, found 526 and 528 (M+NH4, 100%).

Workup

temperatureThe reaction is cooled
extractionextracted with Et2O
dry with materialThe organic layer is dried (Na2SO4
customthe solvent is removed in vacuo
customto afford crude product that
customis absorbed on silica gel
custompurified by flash chromatography

Sources & evidence

ORD record: ord-dc51122ea34d4db490f8fbde7ffa345c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608639B2

Reaction notes

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