Hydrochloric Acid → 3-Bromo-4-chloro-5-fluoropyridine hydrochloride

HRID 524883Notes

Reaction equation

HRID 524883 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[Cl:8].Cl>CCCCC>[ClH:8].[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 709772193-Bromo-4-chloro-5-fluoropyridine

Product 1

HCID 867209403-Bromo-4-chloro-5-fluoropyridine hydrochlorideYield 120.6%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a solution of 3-bromo-4-chloro-5-fluoro-pyridine (7.56 g, 32.18 mmol) in pentane (100 mL) was added hydrogen chloride (2M in ether) (17.7 mL of 2 M, 35.4 mmol). An off-white precipitate formed instantly. The mixture was stirred for 5 minutes then the solid was collected by filtration, washed with pentane and dried by suction to afford the desired product as an off-white solid (4.79 g, 60%). 1H NMR (DMSO-d6) δ 8.77 (s, 1H), 8.75 (s, 1H).

Workup

  1. customAn off-white precipitate formed instantly
  2. filtrationthe solid was collected by filtration
  3. washwashed with pentane
  4. customdried by suction

Sources & evidence

ORD record
ord-c8dea6efc6e74c3a9f924dc42fb3f8c6
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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