Cesium carbonate → HCID 57894121, compound

HRID 1822347Notes

Reaction equation

HRID 1822347 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](Br)[CH:14]=2)=[CH:8][C:7]=1[CH3:20].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:24]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.[Cu]Cl>[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:29][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][C:25]=3[O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[CH:14]=2)=[CH:8][C:7]=1[CH3:20]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 57894155HCID 57894155, compoundHCID 578941923-[4-(3-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

Product 1

HCID 57894121HCID 57894121, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-[4-(3-bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (0.66 g, 2 mmol), 4-chloro-2-(2-fluoro-phenoxy)-phenol (0.3 g, 1.3 mmol), copper(I) chloride (0.06 g, 0.6 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.06 mL, 0.3 mmol), and cesium carbonate (0.82 g, 2.5 mmol) in NMP (10 mL) is heated to 120° C. The reaction is stirred overnight, and then is cooled to room temperature. The reaction is then quenched with 1N aqueous hydrochloric acid and extracted with ethyl ether. The organic is washed with brine, dried over sodium sulfate, filtered, and the solvent removed. The crude is purified by silica gel column chromatography using 9/1 hexanes/ethyl acetate to elute the pure product. The solvent is removed to afford about 0.072 g (11%) of the desired product. 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C29H24ClFO5 506, found 524 (M+NH4, 100%).

Workup

  1. customThe reaction is then quenched with 1N aqueous hydrochloric acid
  2. extractionextracted with ethyl ether
  3. washThe organic is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe crude is purified by silica gel column chromatography
  8. washto elute the pure product
  9. customThe solvent is removed

Sources & evidence

ORD record
ord-44d2dab3f6064420914498a262432a52
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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