Hexane → HCID 49761822, compound

HRID 746830Notes

Reaction equation

HRID 746830 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[Br-].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Zn+].CCCCCC>C1COCC1.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[C:4]([F:9])[CH:3]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178418723HCID 178418723, compound

Product 1

HCID 49761822HCID 49761822, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1-Bromo-3-fluoro-4-iodo benzene (5.0 g, 16.6 mmol), 2-pyridylzinc bromide (7.4 g, 33.2 mmol) were combined in dry THF (100 mL) under argon and Pd(PPh3)4 (1.9 g, 1.6 mmol) was added. The reaction mixture was heated at 70° C. overnight. The reaction mixture was allowed to cool to ambient temperature. TLC analysis showed no starting material present. The reaction mixture was diluted with EtOAc (300 mL), and washed with H2O (3×100 mL), brine (300 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil. The crude product was purified by column chromatography eluting with 1:9 EtOAc:Hexane to afford 2-(4-bromo-2-fluorophenyl)pyridine (2.0 g, 50% yield) as a yellow solid. MS 254.1 (M++H).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with H2O (3×100 mL), brine (300 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a dark oil
  7. customThe crude product was purified by column chromatography
  8. washeluting with 1:9 EtOAc

Sources & evidence

ORD record
ord-9ac3fffc364e40598041b621eb9e751a
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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