4-(Dimethylamino)phenylboronic acid → HCID 58625644, compound

HRID 2236064Notes

Reaction equation

HRID 2236064 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[C:13]([C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([N:27]2[N:31]=[C:30]3[C:32](Br)=[CH:33][CH:34]=[C:35](Br)[C:29]3=[N:28]2)[C:18]=1[OH:38])([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1.[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>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([C:32]2[C:30]3[C:29](=[N:28][N:27]([C:19]4[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:18]=4[OH:38])[N:31]=3)[C:35]([C:6]3[CH:7]=[CH:8][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][CH:5]=3)=[CH:34][CH:33]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 27343444-(Dimethylamino)phenylboronic acidHCID 16726205HCID 16726205, compound

Product 1

HCID 58625644HCID 58625644, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent3×

Conditions

Temperature
95 °C

Procedure

To a 40 mL glass vial, was added 4-(dimethylamino)phenylboronic acid (0.0858 g, 0.520 mmol), 2,4-di-tert-butyl-6-(4,7-dibromo-benzotriazol-2-yl)-phenol (0.1251 g, 0.260 mmol), toluene (0.65 mL), phase transfer catalyst (Aliquat 366®, 60% in toluene, 0.35 mL), tetrakis (triphenylphosphine) palladium in toluene (0.0104 M, 1.0 ml), and 0.8 mL of 2M degassed aqueous potassium carbonate. The vial was heated on an orbital shaker at 95° C. for 20 hours. After cooling to room temperature, methanol was added to the reaction mixture. Yellow crystals of product were collected after filtration and washed with DI water. Photoluminescence spectrometry of a dilute solution of the product in dichloromethane showed strong emission centered at 569 nm.

Workup

  1. customdegassed aqueous potassium carbonate
  2. temperatureAfter cooling to room temperature
  3. additionmethanol was added to the reaction mixture
  4. customYellow crystals of product were collected
  5. filtrationafter filtration
  6. washwashed with DI water

Sources & evidence

ORD record
ord-d7d2132d11184f1a88cfa26bd14cb252
Source dataset
uspto-grants-2010_05
Patent number
US07714099B2

Reaction notes

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