Water → HCID 59556368, compound

HRID 1172677Notes

Reaction equation

HRID 1172677 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Br[CH2:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].O>CN(C)C=O>[F:19][C:17]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([CH2:10][O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

Product 1

HCID 59556368HCID 59556368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

336 μl 2,2,2-Trifluoroethanol were dissolved in 10 ml dimethylformamide. 243 mg sodium hydride were added and the mixture stirred at room temperature for one hour. Then 1.0 g 2-Bromomethyl-4-fluoro-benzonitrile were added in one portion and the reaction mixture was stirred at room temperature for three hours. The reaction mixture was poured on 50 ml water and extracted five times with portion of 25 ml ethyl acetate. The combined organic layers were dried over MgSO4, the solvent removed in vacuo and the resulting residue purified on silica gel with the eluent heptane=>n-heptane:ethyl acetate=4:1 to obtain 750 mg 4-Fluoro-2-(2,2,2-trifluoro-ethoxymethyl)-benzonitrile.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for three hours
  2. extractionextracted five times with portion of 25 ml ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent removed in vacuo
  5. customthe resulting residue purified on silica gel with the eluent heptane=>n-heptane

Sources & evidence

ORD record
ord-f4603db1ff554db78db633d3bc8f7806
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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