Dichloromethane → HCID 67975877, compound

HRID 1053902Notes

Reaction equation

HRID 1053902 reaction equation
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[C:10]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].ClCCl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:10]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3](=[O:9])[CH2:4][CH2:5][C:6]=2[O:7][CH3:8])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 110954262-Bromo-3-methoxycyclopent-2-enone

Product 1

HCID 67975877HCID 67975877, compoundYield 79.1%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 7B (440 mg, 2.303 mmol), 4-tert-butylphenylboronic acid (492 mg, 2.76 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (188 mg, 0.230 mmol) and K2CO3 (637 mg, 4.61 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was stirred at 100° C. for 16 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (30 mL×4). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (on silica gel, eluted with petroleum ether/ethyl acetate=5:1, v/v) to afford the title compound (445 mg, 1.821 mmol, 79% yield) as a white solid. LC/MS (ESI) m/z 245 (M+H)+.

Workup

  1. washwashed with brine (30 mL×4)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (on silica gel
  6. washeluted with petroleum ether/ethyl acetate=5:1

Sources & evidence

ORD record
ord-f19a3ad7faff4dd29cc810ffa74d620b
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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