4-Hexylphenylboronic Acid → 2,9-Dimethyl-4,7-di-(p-hexylphenyl)-1,10-phenanthroline

HRID 570988Notes

Reaction equation

HRID 570988 reaction equation
Br[C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[C:11](Br)=[CH:10][C:9]([CH3:17])=[N:8]3)[N:5]=[C:4]([CH3:18])[CH:3]=1.[CH2:19]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH3:17][C:9]1[CH:10]=[C:11]([C:28]2[CH:29]=[CH:30][C:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:26][CH:27]=2)[C:12]2[C:7](=[C:6]3[C:15](=[CH:14][CH:13]=2)[C:2]([C:28]2[CH:27]=[CH:26][C:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:30][CH:29]=2)=[CH:3][C:4]([CH3:18])=[N:5]3)[N:8]=1

Participants

3

Reactant 2

HCID 41978644-Hexylphenylboronic AcidHCID 105228964,7-Dibromo-2,9-dimethyl-1,10-phenanthroline

Product 1

HCID 680138752,9-Dimethyl-4,7-di-(p-hexylphenyl)-1,10-phenanthroline

Procedure

Starting with 4,7-dibromo-2,9-dimethyl-1,10-phenanthroline, Phen8, (M. Schmittel, H. Ammon Eur. J. Org. Chem. 1998, 785) and the p-hexylphenylboronic acid (commercially available), the ligand Phen9 is synthesized by a Suzuki-coupling.

Workup

  1. customis synthesized by a Suzuki-coupling

Sources & evidence

ORD record
ord-95498c742a2f43e3a588c85032ba20f6
Source dataset
uspto-grants-2015_05
Patent number
US09024026B2

Reaction notes

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