Cesium carbonate → HCID 59010022, compound

HRID 2118096Notes

Reaction equation

HRID 2118096 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][C:17]=1F.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:15]=[CH:16][C:17]=1[O:10][C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1288446-HydroxybenzofuranHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 59010022HCID 59010022, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-benzofuran-6-ol (418.5 mg, 3.1 mmol) in 6 ml of DMF was added 3-Chloro-4-fluorobenzotrifluoride (681.4 mg, 3.4 mmol) and cesium carbonate (1.5 g, 4.7 mmol). The reaction mixture was heated at 80° C. for 2 hours. After cooling to room temperature, it was diluted with ethyl acetate, washed with water (2×) and brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (0-30%) in hexane. The final product was collected as colorless oil. 1H NMR (CDCl3, δ ppm): 6.8 (s, 1H), 7.0 (two d, 2H), 7.2 (s, 1H), 7.4 (d, 1H), 7.6 (d, 1H), 7.7 (s, 1H), 7.8 (s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (2×) and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with ethyl acetate (0-30%) in hexane
  8. customThe final product was collected as colorless oil

Sources & evidence

ORD record
ord-f73384b89ac14ed890fd47df3b70b66b
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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