Hydrogen Bromide → 2-Bromo-1-(5-bromopyridin-2-YL)ethanone

HRID 589175Notes

Reaction equation

HRID 589175 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BrH:11].O.BrBr>C(O)(=O)C>[Br:11][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24408BromineHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 236247072-Bromo-1-(5-bromopyridin-2-YL)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-(5-bromopyridin-2-yl)ethanone (200 mg, 1.0 mmol) was dissolved in Acetic acid (50 mL) and HBr in Acetic acid (48% solution, 280 uL) was added along with water (100 uL). Warmed to 70 C and added Bromine (51.5 uL, 1.0 mmol) and stirred for 1 hour. The reaction was concentrated to give the desired product (280 mg) containing a small amount of dibrominated product. This material was used as is.

Workup

  1. temperatureWarmed to 70 C
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-9e86130f31db484c83063b1007b90d27
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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