HCID 16726205, compound → HCID 58625637, compound

HRID 2236065Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([N:15]2[N:19]=[C:18]3[C:20](Br)=[CH:21][CH:22]=[C:23](Br)[C:17]3=[N:16]2)[C:6]=1[OH:26])([CH3:4])([CH3:3])[CH3:2]>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>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([N:15]2[N:19]=[C:18]3[C:20]([C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:18]=4)=[CH:21][CH:22]=[C:23]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:17]3=[N:16]2)[C:6]=1[OH:26])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

To a 40 mL glass vial, was added 4-phenylboronic acid (0.127 g, 1.04 mmol), 2,4-di-tert-butyl-6-(4,7-dibromo-benzotriazol-2-yl)-phenol (0.25 g, 0.52 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. Pale 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 no visible emission.

Workup

customdegassed aqueous potassium carbonate
temperatureAfter cooling to room temperature
additionmethanol was added to the reaction mixture
customPale yellow crystals of product were collected
filtrationafter filtration
washwashed with DI water

Sources & evidence

ORD record: ord-06a86d436d364f40ae6bebdda3addfc2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714099B2

Reaction notes

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