Toluene → HCID 57567899, compound

HRID 914534Notes

Reaction equation

HRID 914534 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]([C:20]1[CH:21]=[C:22]2[C:34]3=[C:35]4[C:25](=C(C)C=C(B5OC(C)(C)C(C)(C)O5)[C:29]4=[CH:30][CH:31]=[C:32]3[CH:33]=1)[CH:24]=[CH:23]2)([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].C(O[CH2:56][CH3:57])(=O)C.[C:58]1(C)C=CC=C[CH:59]=1>C(O)C.O.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>[C:16]([C:20]1[CH:21]=[C:22]2[C:34]3=[C:35]4[C:25](=[C:56]([CH3:57])[CH:58]=[C:59]([C:2]5[C:3]6[C:8]([CH:9]=[C:10]7[C:15]=5[CH:14]=[CH:13][CH:12]=[CH:11]7)=[CH:7][CH:6]=[CH:5][CH:4]=6)[C:29]4=[CH:30][CH:31]=[C:32]3[CH:33]=1)[CH:24]=[CH:23]2)([CH3:19])([CH3:18])[CH3:17]

Participants

9

Reactant 5

HCID 1140Toluene2×HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 740629-BromoanthraceneHCID 57567908HCID 57567908, compound

Product 1

HCID 57567899HCID 57567899, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, 5 g (19.4 mmol) of 9-bromoanthracene and 7.73 g (19.4 mmol) of 2-(7-tert-butyl-3-methylpyren-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane were dissolved in a mixed solvent of toluene (240 ml) and ethanol (120 ml). Further, an aqueous solution prepared by dissolving 3.93 g (38.8 mmol) of sodium carbonate in 40 ml of distilled water was added to the resultant, and the whole was stirred at 50° C. for 30 minutes. Tetrakis(triphenylphosphine)palladium (1.57 g, 1.36 mmol) was added to the resultant, and the whole was stirred under heat on a silicone oil bath heated to 90° C. for 3.5 hours. After the resultant had been cooled to room temperature, water, toluene, and ethyl acetate were added to the resultant to separate an organic layer. Further, a water layer was extracted with a mixed solvent of toluene and ethyl acetate (twice), and was then added to the solution of the organic layer that had been separated first. The organic layer was washed with a saturated salt solution, and was then dried with sodium sulfate. The solvent was removed by distillation, and the residue was purified by means of silica gel column chromatography (toluene:heptane 1:3), whereby 6.5 g of Intermediate Compound 1 were obtained.

Workup

  1. customFurther, an aqueous solution prepared
  2. additionwas added to the resultant
  3. stirringthe whole was stirred
  4. temperatureunder heat on a silicone oil bath
  5. temperatureheated to 90° C. for 3.5 hours
  6. temperatureAfter the resultant had been cooled to room temperature
  7. customto separate an organic layer
  8. extractionFurther, a water layer was extracted with a mixed solvent of toluene and ethyl acetate (twice), and
  9. additionwas then added to the solution of the organic layer that
  10. customhad been separated first
  11. washThe organic layer was washed with a saturated salt solution
  12. dry with materialwas then dried with sodium sulfate
  13. customThe solvent was removed by distillation
  14. customthe residue was purified by means of silica gel column chromatography (toluene:heptane 1:3)

Sources & evidence

ORD record
ord-d82e79951dae402392daa16164d0025b
Source dataset
uspto-grants-2011_09
Patent number
US08026664B2

Reaction notes

Loading…