Hydrogen Bromide → 4-(Bromoacetyl)pyridine hydrobromide

HRID 521705Notes

Reaction equation

HRID 521705 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BrH:10].BrBr>C(O)(=O)C>[BrH:10].[Br:10][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 142824-AcetylpyridineHCID 24408Bromine2×

Product 1

HCID 27762394-(Bromoacetyl)pyridine hydrobromideYield 129.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-acetyl pyridine (3.62 g, 29.88 mmol) in acetic acid (30 mL) is added a 48% aqueous solution of hydrogen bromide (5.3 mL, 47.16 mmol). Bromine is added (1.6 mL, 31.14 mmol) drop wise in 4 equal portions. The reaction is stirred for about 2 hours and a solid precipitated. Bromine (1.6 mL, 31.14 mmol) is added and the reaction is stirred overnight. The resulting precipitate is collected, washed with diethyl ether, and dried under vacuum to give the title compound (8.6 g, 102%). 1H NMR (d6-DMSO) δ 9.02 (d, 2H), 8.17 (d, 2H), 5.08 (2H)

Workup

  1. customa solid precipitated
  2. stirringthe reaction is stirred overnight
  3. customThe resulting precipitate is collected
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f2fb85ae64964f4bba84597f1874c5c8
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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