Water → HCID 68210359, compound

HRID 1473735Notes

Reaction equation

HRID 1473735 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1.[CH2:16]([N:18]1[C:30]2[CH:29]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17].C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([N:18]1[C:30]2[CH:29]=[C:28]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=3)[CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11184605HCID 11184605, compoundHCID 67466273HCID 67466273, compound

Product 1

HCID 68210359HCID 68210359, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

3.93 g (15.00 mmol) of 2-bromo-3′-methoxybiphenyl, 5.3 g (16.50 mmol) of 9-ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, and 0.35 g (0.30 mmol) of Pd(PPh3)4 were dissolved in 50 ml of toluene, and 4.77 g (45.00 mmol) of Na2CO3 was put into 25 ml of distilled water and then refluxed and agitated for 5 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of hexane:MC=7:3 (v/v) to obtain 3.90 g of 9-ethyl-2-(3′-methoxybiphenyl-2-yl)carbazole (yield 69%).

Workup

  1. temperaturerefluxed
  2. extractionextraction
  3. filtrationfiltering

Sources & evidence

ORD record
ord-090ce71be3c84e56877aa1bfdfa1db19
Source dataset
uspto-grants-2015_04
Patent number
US09017829B2

Reaction notes

Loading…