Hydrogen Bromide → 3-(2-Bromoacetyl)pyridine hydrobromide

HRID 521704Notes

Reaction equation

HRID 521704 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:9])[CH3:8])[CH:2]=1.[BrH:10].BrBr>C(O)(=O)C.C(OCC)C>[BrH:10].[Br:10][CH2:8][C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:9]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 95893-AcetylpyridineHCID 24408Bromine

Product 1

HCID 27762343-(2-Bromoacetyl)pyridine hydrobromideYield 132.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

To a vigorously stirred solution of 1-(3-pyridinyl)-ethanone (7.2 mL, 65.44 mmol) in acetic acid (65 mL) and a 48% aqueous solution of hydrogen bromide (11 mL, 97.88 mmol) at 0° C. is added bromine (3.5 mL, 68.11 mmol) drop wise. The reaction is warmed to 40° C. with vigorous stirring and stirred for 2 hours. The reaction is then warmed to 75° C. and is stirred for 2 hours. The reaction mixture is cooled to room temperature and diluted with diethyl ether. The resulting precipitate is collected, washed with diethyl ether, and dried under vacuum to give the title compound as a white crystalline solid (18.27 g, 99%). 1H NMR (d6-DMSO) δ 14.53-14.47 (m, 1H), 9.35 (d, J=1.5 Hz, 1H), 9.01 (d, J=4.9 Hz, 1H), 8.72 (d, J=7.8 Hz, 1H), 7.97-7.91 (m, 1H), 5.09 (s, 2H).

Workup

  1. stirringstirred for 2 hours
  2. temperatureThe reaction is then warmed to 75° C.
  3. stirringis stirred for 2 hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. customThe resulting precipitate is collected
  6. washwashed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-868057b41c294955b5348ee42d2dbb68
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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