1,1,1-Trifluoro-2-propanol → HCID 59214388, compound

HRID 2244630Notes

Reaction equation

HRID 2244630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[F:11][C:12]([F:17])([F:16])[CH:13]([OH:15])[CH3:14].[H-].[Na+].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:15][CH:13]([CH3:14])[C:12]([F:17])([F:16])[F:11])[C:5]#[N:6]

Participants

7

Reactant 4

HCID 97741,1,1-Trifluoro-2-propanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 59214388HCID 59214388, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-4-fluorobenzonitrile (300 mg) and 1,1,1-trifluoro-2-propanol (263 mg) in THF (15 ml) was added 60% NaH (92.5 mg) at 5° C., followed by stirring at room temperature for 2 hours, addition of a saturated NH4Cl solution to complete the reaction, and extraction with EtOAc. The obtained organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography (n-hexane:EtOAc=97:3 to 85:15) to obtain 3-chloro-4-(2,2,2-trifluoro-1-methylethoxy)benzonitrile (435 mg) as a colorless oily substance.

Workup

  1. dry with materialThe obtained organic layer was dried over anhydrous MgSO4
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (n-hexane:EtOAc=97:3 to 85:15)

Sources & evidence

ORD record
ord-175f838f7189456383f343954ea1a906
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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