Sodium Carbonate → Sodium 4-(pyridin-4-yl)benzoate

HRID 1675092Notes

Reaction equation

C(=O)([O-])[O-].[Na+:5].[Na+].B([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)(O)O.Cl.Br[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>O.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Na+].[Na+].[Na+].P(C1C=C(S([O-])(=O)=O)C=CC=1)(C1C=C(S([O-])(=O)=O)C=CC=1)C1C=C(S([O-])(=O)=O)C=CC=1>[N:24]1[CH:25]=[CH:26][C:21]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([O-:16])=[O:15])=[CH:12][CH:11]=2)=[CH:22][CH:23]=1.[Na+:5]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of sodium carbonate (830 g, 7834.20 mmol) in water (6800 mL) was added dropwise over 30 minutes to a stirred suspension of 4-boronobenzoic acid (520 g, 3133.68 mmol), 4-bromopyridine hydrochloride (622 g, 3196.35 mmol) and palladium(II) acetate (1.407 g, 6.27 mmol) in ethanol (2600 mL) and water (3600 mL) at 20° C. The reaction was stirred for 10 minutes then 3,3′,3″-phosphinidynetris(benzenesulfonic acid) trisodium salt (30% w/w solution in water) (36.8 g, 18.80 mmol) was added and the mixture was heated to 85° C. for 4 hours. The reaction mixture was cooled to 55° C. and stirred for 2 hours, then the resulting suspension was stirred at 20° C. for 16 hours. The solid was collected by filtration, washed with acetone (3×1250 mL), and dried in a vacuum oven at 60° C. to afford sodium 4-(pyridin-4-yl)benzoate (690 g, 99%) as a solid.

Workup

temperatureThe reaction mixture was cooled to 55° C.
stirringstirred for 2 hours
stirringthe resulting suspension was stirred at 20° C. for 16 hours
filtrationThe solid was collected by filtration
washwashed with acetone (3×1250 mL)
customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record: ord-1c2092418f664d41bc135f7d80518482
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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