Toluene → HCID 18504279, 화합물

HRID 2227698

반응식

HRID 2227698 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) was prepared by adding butyllithium (0.64 g dissolved in 4 mL hexane) was added into a solution of 4-bromotriphenylamine (3.24 g) in 50 mL tetrahydrofuran at −78° C. The mixture was stirred while the solution temperature warmed up to 10° C. It was cooled again to −78° C. when borolane (2.23 g) was added. The mixture was then stirred at room temperature for 20 hrs and poured into water. The product was extracted with ether, washed with brine, and dried with MgSO4. Solvent was evaporated. The residue was chromatographed on a silica gel column using a hexane/ethyl acetate mixture as eluent (40:1). 2.03 g of the product, 4-diphenylamino-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, was obtained. Then, 4-diphenylamino-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (6.09 g), 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-6d7377c3f58e47d9a31ee1f16c665f37
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06414104B1

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