4-Formylphenylboronic Acid → 4-(4-Bromo-2-pyridyl)benzaldehyde

HRID 1993096Notes

Reaction equation

HRID 1993096 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][N:14]=1>>[Br:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 8171042,4-Dibromopyridine

Product 1

HCID 591319754-(4-Bromo-2-pyridyl)benzaldehyde

Procedure

Alternatively, as illustrated in Scheme 40, Example 2, the phenylboronic acid 40.1 is coupled, as described above, with 2,4-dibromopyridine 40.14 to afford 4-(4-bromo-2-pyridyl)benzaldehyde 40.15. The product is then reacted with a dialkyl mercaptoethyl phosphonate 40.16, the preparation of which is described in Zh. Obschei. Khim., 1973, 43, 2364, to yield the thioether 40.17. Equimolar amounts of the reactants are combined in dimethylformamide at 80° in the presence of potassium carbonate, to effect the displacement reaction.

Sources & evidence

ORD record
ord-a6026fb8bafa4433ad42a17784e6bc5a
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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