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

HRID 1410599Notes

Reaction equation

HRID 1410599 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-b5d59f85210640c48b8152a65a2207fd
Source dataset
uspto-grants-2014_12
Patent number
US08921562B2

Reaction notes

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