1,4-Dioxane → HCID 71254748, compound

HRID 337394Notes

Reaction equation

HRID 337394 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([F:17])([F:16])[C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)C([O:25][CH2:26][CH3:27])=C)CCC.[O:36]1CCO[CH2:38][CH2:37]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:5]1([F:17])[C:6]2[CH:7]=[C:8]([C:37](=[O:36])[CH3:38])[CH:9]=[CH:10][C:11]=2[C:12]2[C:4]1=[CH:3][C:2]([C:26](=[O:25])[CH3:27])=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 596112352,7-Dibromo-9,9-difluorofluorene

Product 1

HCID 71254748HCID 71254748, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of 2,7-dibromo-9,9-difluoro-9H-fluorene (900 mg, 2.500 mmol), Tributyl(1-ethoxyvinyl)tin (3.38 mL, 10.00 mmol) and Pd(Ph3P)4 (289 mg, 0.250 mmol) in 1,4-dioxane (25 mL) were degassed with nitrogen for 10 min then it was heated at 90° C. for overnight under nitrogen. The reaction mixture was cooled to room temperature and 15 mL of 10% HCl was added then stirred for 1 h. The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine. The organics were dried (Na2SO4) and concentrated. The crude material was purified on silica gel using 0-100% ethyl acetate in hexane. The desired fractions were concentrated to give a white solid.

Workup

  1. customwere degassed with nitrogen for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. addition15 mL of 10% HCl was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and brine
  6. dry with materialThe organics were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel using 0-100% ethyl acetate in hexane
  9. concentrationThe desired fractions were concentrated
  10. customto give a white solid

Sources & evidence

ORD record
ord-d03dec20ed1e444a8eeab42d21316cd5
Source dataset
uspto-grants-2014_11
Patent number
US08889726B2

Reaction notes

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