Toluene → HCID 18504279, compound

HRID 1358109Notes

Reaction equation

HRID 1358109 reaction equation
[C:1]1([N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]2[CH:13]=[CH:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:30]1[CH:35]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]=[CH:32][C:31]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:1]1([N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:32]3[CH:33]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:35]=[CH:30][C:31]=3[CH2:41][O:42][C:43](=[O:45])[CH3:44])=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11639307Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amineHCID 185042802-Bromo-1,4-bis(acetyloxymethyl)benzene

Product 1

HCID 18504279HCID 18504279, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

4-Diphenylamino-1-(4,4,5,5-tetramethyl-1,3,2-Dioxaborolan-2-yl)benzene (6.09 g) (prepared by successive reaction of 4-bromo-triphenylamine with butyllithium and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane), 2-bromo-1,4-bis(acetyloxymethyl)benzene (4.9 g), tetrakis(triphenylphosphine)-palladium(0) (0.15 g), toluene (15 mL), and an aqueous solution of sodium carbonate (2M, 25 mL) were mixed under argon. The resulting mixture was stirred at reflux for 2 days, cooled, and poured into water. The aqueous mixture was then extracted with ether. The etheral solution was washed with dilute HCl, brine, dried with magnesium sulfate, and evaporated. The residue was recrystallized in methanol to yield 5.70 g of 2-(4-diphenylamino-phenyl)-1,4-bis(acetyloxymethyl)benzene.

Workup

  1. temperatureat reflux for 2 days
  2. temperaturecooled
  3. extractionThe aqueous mixture was then extracted with ether
  4. washThe etheral solution was washed with dilute HCl, brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. customThe residue was recrystallized in methanol

Sources & evidence

ORD record
ord-b03acb7ee9654658983403b6ea40505a
Source dataset
uspto-grants-2003_07
Patent number
US06593687B1

Reaction notes

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