Bromine → Methyl 4-(5-bromo-6-methoxyquinolin-2-yl)benzoate

HRID 55820Notes

Reaction equation

HRID 55820 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH:7]=[CH:6]2.[Br:23]Br>C(Cl)Cl>[Br:23][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=[N:9]2

Participants

4

Reactant 2

HCID 24408BromineHCID 66980098Methyl 4-(6-methoxyquinolin-2-yl)benzoate

Product 1

HCID 66980100Methyl 4-(5-bromo-6-methoxyquinolin-2-yl)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(6-methoxyquinolin-2-yl)benzoate (630 mg, 2.15 mmol) in DCM (9 mL) was added Br2 (0.3 mL, 6.45 mmol). The reaction mixture was stirred at room temperature overnight. Then the mixture was partitioned with brine and DCM. The precipitate was filtered and dried to give the product as a solid (800 mg, 100%). MS (ESI): m/z=373.0 [M+1]+.

Workup

  1. customThen the mixture was partitioned with brine and DCM
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-37afd7fc6b4b45b6b8ad9511631fe136
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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