Diethyl Ether → Isoquinoline, 4-bromo-7-chloro-, 2-oxide

HRID 1783756Notes

Reaction equation

HRID 1783756 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1.CCOCC>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-:21])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 569733294-Bromo-7-chloroisoquinoline

Product 1

HCID 68900861Isoquinoline, 4-bromo-7-chloro-, 2-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-bromo-7-chloroisoquinoline (3-6)(1 g, 4.12 mmol, 1.0 equiv.) was dissolved in anhydrous CH2Cl2 (8.2 mL) and treated with mCPBA (1.622 g, 9.40 mmol, 2.3 equiv.). The reaction mixture was stirred at room temperature, forming 3-7 as a white precipitate. Following dilution with Et2O, the solid was collected and used without further purification in the next step. LRMS m/z (M+H) 260.1 found, 259.9 required.

Workup

  1. customforming 3-7 as a white precipitate
  2. customthe solid was collected
  3. customused without further purification in the next step

Sources & evidence

ORD record
ord-efc5cfcb18e3442fbfddda25730b794d
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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