Pyridine → tert-Butyl 6-bromopicolinate

HRID 2178234Notes

Reaction equation

HRID 2178234 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(Cl)(=O)=O)=C[CH:2]=1.[Br:12][C:13]1(C(O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][NH:14]1.N1C=CC=CC=1.[C:28](=[O:31])(O)[O-:29].[Na+]>C(O)(C)(C)C>[Br:12][C:13]1[N:14]=[C:15]([C:28]([O:29][C:1]([CH3:11])([CH3:6])[CH3:2])=[O:31])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 210815642-Bromo-picolinic acid

Product 1

HCID 23432991tert-Butyl 6-bromopicolinateYield 79%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

p-Toluenesulfonyl chloride (9.0 g, 47.2 mmol) was added portionwise to a mixture of 2-bromo-picolinic acid (4.02 g, 19.9 mmol) in tert-butanol (36 mL) and pyridine (10.8 mL, 134 mmol) at 0° C. and the mixture was stirred at rt for 14 hours. An aqueous solution of sodium bicarbonate was slowly added. The precipitate was filtered, washed with water and dried in vacuo to provide 4.04 g (79%) of the desired product tert-butyl 6-bromopicolinate (25A): 1H NMR (300 MHz, CDCl3) δ 7.97 (1H, dd), 7.64 (2H, m), 1.62 (9H, s).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3aa7174552bb4255b27d87e46f3b948c
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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