Toluene → HCID 18504279, 화합물

HRID 1358109

반응식

HRID 1358109 반응식
[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

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11639307Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amineHCID 18504280HCID 18504280, 화합물

생성물 1

HCID 18504279HCID 18504279, 화합물수율 75.2%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b03acb7ee9654658983403b6ea40505a
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593687B1

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