Potassium Carbonate → HCID 131727688, compound

HRID 1822085Notes

Reaction equation

HRID 1822085 reaction equation
[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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.C1(C)C=CC=CC=1>[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 131727687HCID 131727687, compound

Product 1

HCID 131727688HCID 131727688, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

At first, a mixture of the 4-(diallylethoxysilyl)bromobenzene (191 mg, 0.61 mmol) obtained in Example 1, Pd(PPh3)4 (21.3 mg, 0.018 mmol), K2CO3 (127 mg, 0.92 mmol), and 4-methoxyphenyl boronic acid (112 mg, 0.74 mmol) was added with dist.toluene (5 mL). Subsequently, the resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 13 hours to obtain a reaction mixture. Thereafter, a salt formed in the reaction mixture was removed by filtering with celite. The solvent was distilled from the organic layer with an evaporator to obtain a crude product. After that, the crude product thus obtained was separated and purified with PTLC (hexane/EtOAc=10/1), and thereby 4-(diallylethoxysilyl)-4′-methoxybiphenyl was obtained (125.4 mg, 60% yield).

Workup

  1. additionwas added with dist
  2. customto obtain a reaction mixture
  3. customThereafter, a salt formed in the reaction mixture
  4. customwas removed
  5. filtrationby filtering with celite
  6. distillationThe solvent was distilled from the organic layer with an evaporator
  7. customto obtain a crude product
  8. customAfter that, the crude product thus obtained
  9. customwas separated
  10. custompurified with PTLC (hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-1dfe305003d247bcbb3adb1e97f7f71a
Source dataset
uspto-grants-2009_10
Patent number
US07608673B2

Reaction notes

Loading…