Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 58396201, compound

HRID 446258Notes

Reaction equation

HRID 446258 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-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC(S(O[CH2:31][CH2:32][Cl:33])(=O)=O)=CC=1>O>[Cl:33][CH2:32][CH2:31][O:14][C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 10796Cesium carbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 58396201HCID 58396201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-nitro-5-(trifluoromethyl)phenol (2.10 g, 10.1 mmol) and cesium carbonate (4.00 g, 12.2 mmol) in acetonenitrile (50 ml) was added 2-chloroethyl p-toluenesulfonate (2.9 g, 12 mmol) slowly. The resulting mixture was stirred at RT for 5 hr, poured into water (100 ml) and then extracted with EtOAc (3×80 ml). The combined organic layer was washed with brine (100 ml) and dried over Na2SO4. Solvent was removed under vacuum and the residue was purified by flash column chromatography on the silica gel (hexane/EtOAc=5 to 25%) to afford the desired compound.

Workup

  1. extractionextracted with EtOAc (3×80 ml)
  2. washThe combined organic layer was washed with brine (100 ml)
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed under vacuum
  5. customthe residue was purified by flash column chromatography on the silica gel (hexane/EtOAc=5 to 25%)

Sources & evidence

ORD record
ord-633a84f13fa5495885a16e8147de5568
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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