2,2,2-Trifluoroethanol → HCID 54370116, compound

HRID 536056Notes

Reaction equation

HRID 536056 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([O:15][CH2:14][C:13]([F:17])([F:16])[F:12])[CH:7]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 54370116HCID 54370116, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-difluoro-1-nitrobenzene (10 g, 62.9 mmol) and 2,2,2-trifluoroethanol (6.29 g, 62.9 mmol) in THF (100 mL) at 25° C. was treated with Cs2CO3 (20.5 g, 62.9 mmol) and stirred for 8 hours before being diluted with the addition of water and extracted with EtOAc. The organic extract was dried (Na2SO4), concentrated, and subjected to flash chromatography (3% EtOAc-petroleum ether) to give 4-fluoro-1-nitro-2-[(2,2,2-trifluoroethyl)oxy]benzene (10 g, 67%) as a yellow solid. MS (m/z) 240.0 (M+H+).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a15807d03235409aa3c8a2cac85a56f5
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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