Ethanol → 5-Bromo-2-phenylpyridine

HRID 1353997Notes

Reaction equation

HRID 1353997 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 693532,5-Dibromopyridine

Product 1

HCID 27628625-Bromo-2-phenylpyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

30 g (0.127 mol) of 2,5-dibromopyridine in suspension in 100 ml of toluene, 15.4 g (0.127 mol) of phenylboronic acid, 4.4 g (0.0038 mol) of tetrakis(triphenylphosphine)palladium, 90 ml of a 2M aqueous solution of sodium carbonate and 4 ml of ethanol are introduced in succession into a 500 ml three-necked flask, and the mixture is heated at 90° C. for 22 h.

Sources & evidence

ORD record
ord-780b2ab212bb487c869fedace53e3e37
Source dataset
uspto-grants-2007_05
Patent number
US07223750B2

Reaction notes

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