2-Chloro-4-fluorobenzonitrile → HCID 17986305, compound

HRID 2233386Notes

Reaction equation

HRID 2233386 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[Cl:21][C:22]1[CH:29]=[C:28](F)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>C(COC)OC>[Cl:21][C:22]1[CH:29]=[C:28]([CH:27]=[CH:26][C:23]=1[C:24]#[N:25])[O:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 1090002-Chloro-4-fluorobenzonitrileHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 17986305HCID 17986305, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium tert-butoxide (5.57 g, 49.68 mmol) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (5.00 g, 24.84 mmol) in glyme (100 ml) and the mixture stirred for 30 min. before addition of 2 chloro-4-fluoro-benzonitrile (7.73 g, 49.68 mmol). The reaction was stirred at room temperature overnight and then partitioned between ethyl acetate (250 ml) and water (200 ml). The organic layer was separated, dried over magnesium sulfate and the solvent evaporated. The residue was purified by flash chromatography eluting with ethyl acetate:isohexane (4:1) to give the subtitle compound as a colourless solid (3.45 g).

Workup

  1. custompartitioned between ethyl acetate (250 ml) and water (200 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate:isohexane (4:1)

Sources & evidence

ORD record
ord-98663181b051448f92def660614d2967
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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