Triethylamine → 2-Fluoro-4-vinylbenzonitrile

HRID 1187012Notes

Reaction equation

HRID 1187012 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=1)(=O)=O.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH:7]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=1)=[CH2:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866473092-(4-Cyano-3-fluorophenyl)ethyl methanesulfonate

Product 1

HCID 219046072-Fluoro-4-vinylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-cyano-3-fluorophenyl)ethyl methanesulfonate (35.0 g, 144 mmol) and triethylamine (50 mL) in DCM (200 mL) was added DBU (50 mL) dropwise to at 0° C. After stirring at room temperature overnight, the solution was diluted with DCM, washed with 1 N HCl and brine, and dried over anhydrous sodium sulphate and concentrated. The residue was purified by column chromatography to give 4-ethenyl-2-fluorobenzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.53˜7.57 (m, 1H), 7.20˜7.26 (m, 2H), 6.64˜6.71 (m, 1H), 5.48˜5.90 (m, 2H).

Workup

  1. washwashed with 1 N HCl and brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-93b960c9dbe94e81ba9fee74bdf79232
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…