Cesium carbonate → HCID 66721612, compound

HRID 1640154Notes

Reaction equation

HRID 1640154 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:27][C@@H:28]1[CH2:32][O:31][C:30]([CH3:34])([CH3:33])[O:29]1)(=O)=O>CN(C=O)C>[CH3:33][C:30]1([CH3:34])[O:29][C@H:28]([CH2:27][O:14][C:6]2[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:32][O:31]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 11832269HCID 11832269, compound

Product 1

HCID 66721612HCID 66721612, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 3-nitro-5-(trifluoromethyl)phenol (0.658 g, 3.17 mmol), cesium carbonate (3.10, 9.52 mmol) and [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate (1.00 g, 3.49 mmol) in DMF (10 mL) was heated at 60° C. for 56 h. The reaction mixture was allowed to cool to rt and filtered. The filtrate was diluted with EtOAc and washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give (4R)-2,2-dimethyl-4-{[3-nitro-5-(trifluoromethyl)-phenoxy]methyl}-1,3-dioxolane (770 mg, 75%) of as pale yellow oil. 1H NMR (400 MHz,CDCl3, HCl salt) δ: 8.10 (s, 1H), 7.94-7.97 (m, 1H), 7.51 (s, 1H), 4.49-4.56 (m, 1H), 4.09-4.23 (m, 3H), 3.92 (q, 1H), .1.45 (s, 3H), and 1.41 (s, 3H).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7f4411b3ecb8457291e6b714b6bce713
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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