Phenylboronic Acid → HCID 58175620, compound

HRID 2041827Notes

Reaction equation

HRID 2041827 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([CH2:21][CH3:22])[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:21]([C:4]1[CH:3]=[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:22]

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 58175692HCID 58175692, compound

Product 1

HCID 58175620HCID 58175620, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A 2-necked 250 mL round-bottom flask was charged with 1-(4-bromo-2,6-diethylphenyl)-2-phenyl-1H-imidazole (6.75 g, 19 mmol), phenylboronic acid (4.63 g, 38 mmol), dicyclohexyl (2′,6′-dimethoxy-biphenyl-2-yl)phosphine (0.312 g, 0.76 mmol), and tripotassium phosphate monohydrate (12.1 g, 51 mmol) in 100 mL of toluene and 10 mL of water. The mixture was degassed by bubbling nitrogen directly into solution for 20 min. Pd2(dba)3 was added and the reaction heated to reflux overnight under nitrogen. The organic layer was separated and solvent was evaporated. The material was column purified by silica gel chromatography eluting with 20% ethyl acetate/hexanes. 5.5 g (82% yield) of product was obtained.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen directly into solution for 20 min
  3. additionPd2(dba)3 was added
  4. temperaturethe reaction heated
  5. temperatureto reflux overnight under nitrogen
  6. customThe organic layer was separated
  7. customsolvent was evaporated
  8. custompurified by silica gel chromatography
  9. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9e836fed228a4d9a97f542e231c40cca
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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