Pyridine → tert-Butyl 6-bromopicolinate

HRID 1896584Notes

Reaction equation

HRID 1896584 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-05ebd5e184f24c2981849bc5b14d4f4c
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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