Tetrabutylammonium Fluoride → 5-Ethynyl-2-fluorobenzonitrile

HRID 1752543Notes

Reaction equation

HRID 1752543 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-94c1e07c19da49bf9ea3158a4bc7d157
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

Loading…