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

HRID 628894Notes

Reaction equation

HRID 628894 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-da14baa349f240b2acedfc6b9b127195
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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