Tetrahydrofuran → 4-Bromo-3-methoxyquinolin-3-yl-diazonium tetrafluoroborate

HRID 1787679Notes

Reaction equation

HRID 1787679 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[Br:12])=[CH:9][C:8](OC)=[CH:7][CH:6]=2.[F:15][B-:16]([F:19])([F:18])[F:17].[N:20]#[O+].C1[CH2:26][O:25]CC1>>[F:15][B-:16]([F:19])([F:18])[F:17].[Br:12][C:11]1[C:2]([N+:1]#[N:20])([O:25][CH3:26])[CH2:3][N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11137142Nitrilooxonium tetrafluoroborateHCID 684539074-Bromo-6-methoxyquinolin-3-amine

Product 1

HCID 1317273704-Bromo-3-methoxyquinolin-3-yl-diazonium tetrafluoroborateYield 76%

Conditions

Temperature
-2.5 °C

Procedure

3-Amino-4-bromo-6-methoxyquinoline (18.4 g, 0.0727 mole) was dissolved in dry THF (250 mL) and the solution was cooled to −8° C. (EtOH-ice bath). Nitrosonium tetrafluoroborate (9.34 g, 0.08 mole) was added in portions over 10 min, keeping the temperature less than −2° C. The mixture was stirred at −5 to 0° C. for 30 min, then the yellow precipitate was filtered off and washed sequentially with cold THF and hexane. Drying in vacuo gave the title compound (19.4 g, 76%) an insoluble orange-yellow solid.

Workup

  1. customthe temperature less than −2° C
  2. filtrationthe yellow precipitate was filtered off
  3. washwashed sequentially with cold THF and hexane
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-30bce440e33f465fba6e680951650d33
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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