Bromine → HCID 22139688, compound

HRID 1825862Notes

Reaction equation

HRID 1825862 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[Br:14]Br>C(Cl)Cl>[Br:14][C:8]1[C:7]([O:12][CH3:13])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([Cl:1])=[N:3]2

Participants

4

Reactant 2

HCID 24408BromineHCID 836472-Chloro-6-methoxyquinoline

Product 1

HCID 22139688HCID 22139688, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-6-methoxyquinoline (4.4 g, 22 mmol) in CH2Cl2 (60 mL) was treated by slow addition of Br2 (3.5 mL, 11 g, 68 mmol). After 14 hours, the mixture was partitioned between NaCl and CH2Cl2. The aqueous layer was extracted with CH2Cl2. The organic layer was worked-up. HPLC (1:10 EtOAc/hexane) gave 6.1 g (99%) of 5-bromo-2-chloro-6-methoxyquinoline as a light yellow solid, (M+) 273(100).

Workup

  1. customthe mixture was partitioned between NaCl and CH2Cl2
  2. extractionThe aqueous layer was extracted with CH2Cl2

Sources & evidence

ORD record
ord-fbd3d71221644960a97818c926fd64cc
Source dataset
uspto-grants-2006_05
Patent number
US07049325B2

Reaction notes

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