Triphenylphosphane dibromide → 4-Bromo-6-chloro-8-methylquinoline

HRID 2090045Notes

Reaction equation

HRID 2090045 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.[Br-:14].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:14][C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 12890784Triphenylphosphane dibromideHCID 178426082HCID 178426082, compound

Product 1

HCID 170400714-Bromo-6-chloro-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-4-hydroxy-8-methylquinoline (1.9 g, 9.8 mmol) and triphenylphosphine dibromide (6.2 g, 14.7 mmol) in acetonitrile (50 mL) was refluxed for 2 hours. The mixture was allowed to cool to room temperature then concentrated. The residue was purified by silica gel chromatography eluting with 0-10% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.67 (d, J=4.7 Hz, 1H); 8.06 (d, J=2.2 Hz, 1H); 7.71 (d, J=4.6 Hz, 1H); 7.58 (s, 1H); 2.79 (s, 3H); LC1: 1.88 min. (M+H) 256.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationthen concentrated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 0-10% EtOAc/hexanes

Sources & evidence

ORD record
ord-4126e585241548c5ae153fe2887b0eff
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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