Allyltributylstannane → 2-Chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile

HRID 2173218Notes

Reaction equation

HRID 2173218 reaction equation
[Cl:1][C:2]1[C:9](I)=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[Li+].[Cl-]>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:9]([CH2:14][CH:13]=[CH2:12])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 675158122-Chloro-6-fluoro-3-iodobenzonitrile

Product 1

HCID 675161222-Chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-6-fluoro-3-iodobenzonitrile (800 mg, 2.85 mmol), allyltributylstannane (1.245 mg, 3.761 mmol), LiCl (431 mg, 10.3 mmol) and Pd(PPh3)4 (100 mg) in 50 mL toluene was heated at 100° C. overnight. Cooled to rt. and diluted with 50 mL EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified via prep-TLC (ethyl acetate/Pet ether=1:5) to give 2-chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.37˜7.41 (m, 1H), 7.01˜7.06 (m, 1H), 5.78˜5.87 (m, 1H), 4.99˜5.12 (m, 2H), 3.44 (d, J=6.3 Hz, 2H).

Workup

  1. temperatureCooled to rt
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified via prep-TLC (ethyl acetate/Pet ether=1:5)

Sources & evidence

ORD record
ord-89c893a53f09414da9ab3ace5c8ace6c
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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