Tetrabutylammonium Fluoride → 5-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

HRID 734800Notes

Reaction equation

HRID 734800 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([C:26]#[C:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[CH:30][N:29]=1)(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:31]2[CH:32]=[C:33]([F:34])[C:28]([C:27]#[CH:26])=[N:29][CH:30]=2)=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 690583282-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine

Product 1

HCID 600554165-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.14 g (3.61 mmol) of TBAF was added at RT to a solution of 1.25 g (3.61 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine in 30 mL of DCM and the mixture was stirred for 2 hours. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue was stirred with PE, the precipitate was filtered off, washed with PE, and dried in the air. Yield: 0.72 g (86% of theoretical); C13H7ClFN (M=231.653); calc.: molpeak (M+H)+: 232/234 (Cl); found: molpeak (M+H)+: 232/234 (Cl); HPLC-MS: 5.81 minutes (method B).

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down in vacuo
  4. stirringThe residue was stirred with PE
  5. filtrationthe precipitate was filtered off
  6. washwashed with PE
  7. customdried in the air
  8. custom5.81 minutes (method B)

Sources & evidence

ORD record
ord-edf9bac4da0745ca9fd47e96455dba3f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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