Cyclopropylacetylene → HCID 68722130, compound

HRID 1752551Notes

Reaction equation

HRID 1752551 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH:11]1([C:14]#[CH:15])[CH2:13][CH2:12]1>C(N(CC)CC)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:11]1([C:14]#[C:15][C:2]2[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=2)[C:7]#[N:8])[CH2:13][CH2:12]1

Participants

7

Reactant 2

HCID 138823CyclopropylacetyleneHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 68722130HCID 68722130, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-2-fluorobenzonitrile (3.06 g, 15.3 mmol), dichlorobis(triphenylphosphine)palladium(II) (478 mg, 0.681 mmol), and copper(I) iodide (165 mg, 0.866 mmol) were combined in triethylamine (15 mL) under an inert atmosphere of nitrogen. Cyclopropylacetylene (1.8 mL) was added, and the mixture was heated to 60° C. until it turned to a black solid. The mixture was diluted with methylene chloride and washed with 1 N hydrochloric acid. 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. MS (ESI+) m/z 319.0 (M+H)+.

Workup

  1. washwashed with 1 N hydrochloric acid
  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-30e855ec67ca470f9711a291223cd0f3
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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