Hydrogen Bromide → 2-bromo-1-(6-bromopyridin-3-yl)ethanone

HRID 1776046Notes

Reaction equation

HRID 1776046 reaction equation
[Br:1]Br.[Br:3][C:4]1[N:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.Br>C(Cl)Cl>[Br:1][CH2:11][C:10]([C:7]1[CH:8]=[N:9][C:4]([Br:3])=[CH:5][CH:6]=1)=[O:12]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 156681955-Acetyl-2-bromopyridine

Product 1

HCID 108502672-bromo-1-(6-bromopyridin-3-yl)ethanoneYield 116.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of bromine (4 g, 25 mmol) in DCM (10 mL) was added drop wise over 5 min to a cooled (0° C.) solution of 1-(6-bromo-pyridin-3-yl)-ethanone (5 g, 25 mmol) and HBr (48%, 0.2 mL). The cooling bath was removed 40 min later and stirring was continued at RT for 66 h. The solid that formed was filtered, washed with DCM and dried at room temperature to give the impure title intermediate (8.1 g) as a yellow solid. 1H NMR (CD3OD, 400 MHz) δ (ppm): 8.96 (m, 1H), 8.28-8.25 (m, 1H), 7.82-7.79 (m, 1H), 4.7 (s, 2H).

Workup

  1. customThe cooling bath was removed 40 min later
  2. customThe solid that formed
  3. filtrationwas filtered
  4. washwashed with DCM
  5. customdried at room temperature

Sources & evidence

ORD record
ord-40c158e8f1f54fd39c8620f9c0d327a5
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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