Stannane, tributyl(1-ethoxyethenyl)- → 1-[4-Fluoro-3-(hydroxyphenylmethyl)phenyl]ethanone

HRID 1365065Notes

Reaction equation

HRID 1365065 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:22]([O:24]CC)=[CH2:23])CCC>[Cl-].C([N+](CC)(CC)CC)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.C(#N)C>[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:22](=[O:24])[CH3:23])=[CH:7][C:6]=1[CH:8]([OH:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 54595143HCID 54595143, compound

Product 1

HCID 577324311-[4-Fluoro-3-(hydroxyphenylmethyl)phenyl]ethanone

Reagents, catalysts & solvents 3

HCID 5946Tetraethylammonium ChlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A 5 mL microwave tube was charged with (5-bromo-2-fluorophenyl)-(phenyl)methanol (1 eq), tributyl-(1-ethoxyvinyl)tin (1 eq), tetraethylammonium chloride (3 eq), bis(triphenylphosphine)palladium(II) chloride (10 mol %) and acetonitrile (3.5 mL). The reaction was heated to 150° C. for one hour using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered and then concentrated to an oil. Purification by silica gel chromatography provided 1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone as an oil. H1 NMR (d6-dmso): 8.16 (dd, 1H), 7.89 (m, 1H), 7.18-7.34 (m, 6H), 6.14 (d, 1H), 5.93 (d, 1H), 2.53 (s, 3H).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-18d3697e92a74718b348c64d4ced7a25
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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