1-Fluoro-3-iodobenzene → HCID 89760791, compound

HRID 523114Notes

Reaction equation

HRID 523114 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]=[O:11])=[CH:2]1.[Mg+2].[Cl-].[Cl-].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=1>C1COCC1.[NH4+].[Cl-].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[F:15][C:16]1[CH:17]=[C:18]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]=2[CH:10]=[O:11])[CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 3

HCID 707251-Fluoro-3-iodobenzeneHCID 2273281-Benzothiophene-3-carbaldehydeHCID 5360315Magnesium Chloride

Product 1

HCID 89760791HCID 89760791, compoundYield 76.1%

Reagents, catalysts & solvents 4

HCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
25 °C

Procedure

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with 1-benzothiophene-3-carbaldehyde (163 mg, 1 mmol) in anhydrous THF (1 ml). After adding (TMP)2Zn.MgCl2 (3.16 ml, 1.2 mmol) at 25° C., the mixture is stirred for 1 h, then a solution of 1-fluoro-3-iodobenzene (311 mg, 1.4 mmol), bis(dibenzylideneacetone)palladium(0) (17 mg, 3 mol %) and tri-2-furylphosphine (14 mg, 6 mol %) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25° C. overnight. For workup, the mixture is diluted with aqueous sat. NH4Cl solution (30 ml) and extracted with ethyl acetate (3×30 ml). After the combined organic phases have been dried over Na2SO4, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane:ethyl acetate), the desired compound (195 mg, 76% of theory) was obtained as a colourless crystalline product.

Workup

  1. additionA dry, argon-filled Schlenk tube with a magnetic stirrer bar
  2. additionAfter adding (TMP)2Zn
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialAfter the combined organic phases have been dried over Na2SO4
  5. distillationthe solvent has been distilled off
  6. custompurification

Sources & evidence

ORD record
ord-5cde419c9a544f88a8a8b7072edd660f
Source dataset
uspto-grants-2016_05
Patent number
US09334292B2

Reaction notes

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