4-Chlorotoluene → HCID 10130667, compound

HRID 227846Notes

Reaction equation

HRID 227846 reaction equation
CC([O-])(C)C.[Na+].[CH2:7]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10].Cl[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:7]([N:11]([CH2:12][CH2:13][CH2:14][CH3:15])[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 78104-ChlorotolueneHCID 8148DibutylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 10130667HCID 10130667, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (2.3 mg, 0.0025 mmol, 0.05 mol % Pd), 2 [Example 1] (2.9 mg, 0.0075 mmol, 0.075 mol %), and NaOt-Bu (1.34 g, 13.9 mmol). Toluene (10 mL), di-n-butylamine (2.00 mL, 11.9 mmol), and 4-chlorotoluene (1.18 mL, 10.0 mmol) were added and the mixture was degassed using three freeze-pump-thaw cycles. The reaction vessel was placed under argon, sealed with a teflon screw cap, and stirred in a 100° C. oil bath for 20 h after which time GC analysis showed the aryl halide had been completely consumed. The reaction mixture was cooled to room temperature, diluted with ether (100 mL) and extracted with 1 M HCl (3×100 mL). The combined aqueous acid phase was basified with 3N NaOH, then extracted with ether (3×150 mL). The ethereal extracts were dried over anhydrous sodium sulfate, filtered and concentrated to afford 2.01 g (95%) of a pale yellow oil.

Workup

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customthe mixture was degassed
  3. customsealed with a teflon
  4. customscrew cap
  5. customhad been completely consumed
  6. temperatureThe reaction mixture was cooled to room temperature
  7. additiondiluted with ether (100 mL)
  8. extractionextracted with 1 M HCl (3×100 mL)
  9. extractionextracted with ether (3×150 mL)
  10. dry with materialThe ethereal extracts were dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-efcfe954c4784f949c381312cea752e2
Source dataset
uspto-grants-2009_07
Patent number
US07560582B2

Reaction notes

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