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

HRID 1411364Notes

Reaction equation

HRID 1411364 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-ae1663aa076e4a4da10ba3a0910a2dd7
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

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