Sodium Hydroxide → Emd-50929

HRID 48468Notes

Reaction equation

HRID 48468 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[OH-].[Na+]>[Pd].O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 887075-Bromonicotinic acidHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 11378949Emd-50929

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1.38 kg of 5-bromonicotinic acid, 1.10 kg of 4-fluorobenzeneboronic acid and 0.40 kg of Pd/activated carbon (5%) are introduced into 8.5 liters of water. The black suspension is rendered alkaline using 1.39 kg of 32% sodium hydroxide solution and warmed to 100° C. After 4 hours, the mixture is subjected to conventional work-up, giving 5-(4-fluorophenyl)nicotinic acid.

Sources & evidence

ORD record
ord-471ca8150fbd4c65ab045f4e7161b78a
Source dataset
uspto-grants-2004_03
Patent number
US06703509B2

Reaction notes

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