Tetrabutylammonium Fluoride → 5-Ethynyl-2-fluorobenzonitrile

HRID 240755Notes

Reaction equation

HRID 240755 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][Si](C)(C)C)=[CH:24][C:21]=1[C:22]#[N:23]>O1CCCC1.C(Cl)Cl>[C:28]([C:25]1[CH:26]=[CH:27][C:20]([F:19])=[C:21]([CH:24]=1)[C:22]#[N:23])#[CH:29]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 593053312-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

Product 1

HCID 534292955-Ethynyl-2-fluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 70 mL) was added to a solution of Example 62A (5.05 g, 23.2 mmol) in tetrahydrofuran (50 mL) and allowed to stir for 20 minutes. The mixture was diluted with methylene chloride and washed with water. The organic layer was absorbed on silica gel and purified by silica gel chromatography eluting with a gradient of 5-40% ethyl acetate in hexanes to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.13 (dd, J=6.27, 2.20 Hz, 1H) 7.82-7.95 (m, 1H) 7.56 (t, J=8.99 Hz, 1H) 4.40 (s, 1H).

Workup

  1. washwashed with water
  2. customThe organic layer was absorbed on silica gel
  3. custompurified by silica gel chromatography
  4. washeluting with a gradient of 5-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7496bea3697b41a4a2e0262d9851f016
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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