Hydrogen Bromide → HCID 20475367, compound

HRID 2295396Notes

Reaction equation

HRID 2295396 reaction equation
[CH3:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:4][C:5]([CH2:8]O)=[CH:6][CH:7]=1.[BrH:16].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)C>[CH3:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:4][C:5]([CH2:8][Br:16])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 20475365HCID 20475365, compound

Product 1

HCID 20475367HCID 20475367, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

0.9 g (4.5 mmols) of 3-methyl-6-hydroxymethyl-2,2'-bipyridine are boiled under reflux for 6 hours, together with 5 ml of 62% hydrobromic acid. After cooling, 10 ml of water and 20 ml of diethyl ether are added. The water phase is rendered alkaline with potassium carbonate, separated from the ether phase and washed with a further 10 ml of diethyl ether. The combined ether phases are dried over sodium sulfate and concentrated to dryness in vacuo (maximum bath temperature: 30° C.). 1.16 g (98% of theory) of 3-methyl-6-bromomethyl-2,2'-bipyridine remains as an oily product which decomposes at room temperature, giving a red colouration, and crystallises at 0° C. The 3-methyl-6-bromomethyl-2,2'-bipyridine is immediately used further.

Workup

  1. temperatureAfter cooling
  2. customseparated from the ether phase
  3. washwashed with a further 10 ml of diethyl ether
  4. dry with materialThe combined ether phases are dried over sodium sulfate
  5. concentrationconcentrated to dryness in vacuo (maximum bath temperature: 30° C.)
  6. customdecomposes at room temperature
  7. customgiving a red colouration
  8. customcrystallises at 0° C

Sources & evidence

ORD record
ord-37c465cd978a498f9170c404fe5d5797
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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