Water → HCID 67057696, compound

HRID 1988136Notes

Reaction equation

HRID 1988136 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[CH2:10]([Sn](CCCC)(CCCC)C=C)[CH2:11]CC.CCOCC.O>CN(C=O)C.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:10]=[CH2:11])=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 81998TributylvinyltinHCID 27250061-Bromo-2-fluoro-4-iodobenzene

Product 1

HCID 67057696HCID 67057696, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-bromo-2-fluoro-4-iodo-benzene (1 g, 3.32 mmol), tributyl(vinyl)tin (0.97 mL, 3.32 mmol) and dichlorobis(triphenylphosphine)palladium(II) (116 mg, 0.17 mmol) in anhydrous DMF (3 mL) was heated in a microwave reactor to 160° C. for 5 minutes. Ether (20 mL) and H2O (5 mL) were added and partitioned. The organic layer was washed with water, brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with hexanes to provide the title compound as a colorless oil (360 mg, 54%). 1H NMR (300 MHz, CDCl3) δ 5.33 (d, J=9 Hz, 1 H), 5.76 (d, J=18 Hz, 1 H), 6.63 (dd, J=18 Hz, J=9 Hz, 1 H), 7.05 (dd, J=9 Hz, J=1 Hz, 1 H), 7.16 (dd, J=9 Hz, J=1 Hz, 1 H), 7.49 (t, J=9 Hz, 1 H); (DCl/NH3) m/z 201 (M+H)+.

Workup

  1. custompartitioned
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-0a7dffacd4784d76b527856328af1bfb
Source dataset
uspto-grants-2009_06
Patent number
US07553964B2

Reaction notes

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