1,4-Dioxane → 1,1'-(Anthracene-2,6-diyl)diethanone

HRID 520362Notes

Reaction equation

HRID 520362 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9](Br)=[CH:8][CH:7]=3)[CH:3]=1.C([O:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21])C.[O:35]1CCO[CH2:37][CH2:36]1>C(Cl)Cl.Cl.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>[CH:3]1[C:4]2[C:13](=[CH:12][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[C:9]([C:36](=[O:35])[CH3:37])[CH:10]=3)[CH:14]=[CH:15][C:2]=1[C:20](=[O:19])[CH3:21]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 220589062,6-Dibromoanthracene

Product 1

HCID 866900841,1'-(Anthracene-2,6-diyl)diethanone

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,6-dibromoanthracene (1.2 g, 3.57 mmol) in 1,4-dioxane (20 mL) was added 1-ethoxyvinyltri-n-butyltin (3.65 mL, 10.71 mmol) under N2. Then Pd(PPh3)2Cl2 (0.251 g, 0.357 mmol) was added. The reaction mixture was heated at 100° C. for 16 h then cooled to rt and diluted with DCM and 1.5 N HCl. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over Na2SO4 and concentrated. The crude was purified by Combiflash Isco (Silica gel, 12 g, Redisep, 0.5% MeOH in CHCl3) and the resulting product was washed with petroleum ether to yield 1,1′-(anthracene-2,6-diyl)diethanone (600 mg) as a yellow solid. 1H NMR (CDCl3, δ=7.26 ppm, 400 MHz): δ 8.67 (s, 2H), 8.61 (s, 2H), 8.44-8.04 (m, 4H), 2.78 (s, 6H).

Workup

  1. temperaturethen cooled to rt
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by Combiflash Isco (Silica gel, 12 g, Redisep, 0.5% MeOH in CHCl3)
  7. washthe resulting product was washed with petroleum ether

Sources & evidence

ORD record
ord-c2bbb4f463704ced904f31e20b21f46b
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…