Acetonitrile → 1-(2-fluoro-5-methylphenyl)-3-(tetrahydro-2H-pyran-2-yloxy)-1-propyne

HRID 1093385Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[C:17]#[CH:18].C(#N)C>[Cl-].[Na+].O.CC#N.CC#N.Cl[Pd]Cl.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH3:9])=[CH:3][C:2]=1[C:18]#[C:17][CH2:16][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-bromo-4-fluorotoluene (10.0 g), cesium carbonate (45.0 g), 2-(2-propynyloxy)tetrahydropyran (11.2 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.51 g), bis(acetonitrile)palladium(II) dichloride (274 mg) and acetonitrile (250 ml) was stirred at 90° C. for 11 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-95:5) to give the object product (8.32 g) as a pale-brown oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-95:5)

Sources & evidence

ORD record: ord-91fa2044eb65491d9106fee2a1efd413
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129361B2

Reaction notes

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