Cesium carbonate → HCID 59010060, compound

HRID 2118103Notes

Reaction equation

HRID 2118103 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][C:18]=1F.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]([F:21])([F:22])[F:23])[CH:16]=[CH:17][C:18]=1[O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 70206596-Hydroxy-1-indanone

Product 1

HCID 59010060HCID 59010060, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 6-hydroxyindan-1-one (1.48 g, 10 mmol) in 30 ml of DMF was added 3-chloro-4-fluorobenzotrifluoride (2.46 g, 12 mmol) and cesium carbonate (8.40 g, 25 mmol). The reaction mixture was heated at 80° C. for 12 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water (2×) and brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with ethyl acetate (2-40%) in hexane. The final product was collected as brownish yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (2×) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with ethyl acetate (2-40%) in hexane
  8. customThe final product was collected as brownish yellow oil

Sources & evidence

ORD record
ord-c0b183d379674749a6acea2a64660e5c
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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