Triethylamine → 2-Chloro-6-fluoro-3-vinylbenzonitrile

HRID 1502049Notes

Reaction equation

HRID 1502049 reaction equation
Br[C:2]1[C:3]([Cl:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:12](N(CC)CC)[CH3:13]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.C(O)C>[Cl:11][C:3]1[C:2]([CH:12]=[CH2:13])=[CH:9][CH:8]=[C:7]([F:10])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 712393913-Bromo-2-chloro-6-fluorobenzonitrile

Product 1

HCID 867270812-Chloro-6-fluoro-3-vinylbenzonitrile

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 702EthanolSolvent

Procedure

3-Bromo-2-chloro-6-fluorobenzonitrile (15.4 g, 65.6 mmol), potassium vinyl trifluoroborate (17.6 g, 131 mmol), triethylamine (18.3 mL, 131 mmol) and PdCl2(dppf)-CH2Cl2 adduct (2.68 g, 3.28 mmol) were added to ethanol (75 mL) then degassed and heated at reflux for 3 h. The reaction was diluted with ethyl acetate and washed with brine, dried and evaporated to dryness. The product was purified by chromatography through a 330 g ISCO Redi-Sep column with 10% ethyl acetate/hexane solvent system to yield 2-chloro-6-fluoro-3-vinylbenzonitrile.

Workup

  1. customthen degassed
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. additionThe reaction was diluted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. customevaporated to dryness
  8. customThe product was purified by chromatography through a 330 g ISCO Redi-Sep column with 10% ethyl acetate/hexane solvent system

Sources & evidence

ORD record
ord-34985cea81694bb2ac45f05de13cf378
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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