Acetic Acid → 3,5-Dibromo-2-methoxypyridine

HRID 2283457Notes

Reaction equation

HRID 2283457 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.C([O-])(=O)C.[Na+].C(O)(=O)C>CCOCC>[Br:1][C:6]1[C:7]([O:10][CH3:11])=[N:8][CH:9]=[C:4]([Br:3])[CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 27348955-Bromo-2-methoxypyridine

Product 1

HCID 135677523,5-Dibromo-2-methoxypyridineYield 62.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Bromine (17.8 g, 111 mmol) was added to a solution of 5-bromo-2-methoxypyridine (12.0 g, 63.8 mmol), sodium acetate (5.23 g, 63.8 mmol), and acetic acid (65 mL). The mixture was stirred at 80° C. for 4 h and then at room temperature for 12 h. The mixture was diluted with ether and washed with water, sodium bicarbonate and hypo solution. The organic layer was dried over sodium sulphate, filtered and concentrated. Purification by chromatography using 1-5% ethyl acetate in pet ether provided 10.6 g of the desired compound: 1H NMR (300 MHz, DMSO-d6) 8.20-8.40 (m, 2H), 3.92 (s, 3H).

Workup

  1. waitat room temperature for 12 h
  2. washwashed with water, sodium bicarbonate and hypo solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-63f930dc593d42478df5d835550fd53d
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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