Nitrilooxonium tetrafluoroborate → 7-Fluoro-2-nitronaphthalene

HRID 1270774Notes

Reaction equation

HRID 1270774 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](N)=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:15][B-](F)(F)F.N#[O+]>ClCCl>[F:15][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 154071007-Nitro-2-aminonaphthalene

Product 1

HCID 232353787-Fluoro-2-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture 7-nitro-2-aminonaphthalene (1 g, 5.31 mmol) and nitrosonium tetrafluoroborate (931 mg, 7.97 mmol) in dichloromethane (10 mL) is stirred at room temperature for 12 hours and at 110° C. for 1 hour. After cooling to room temperature, the reaction mixture is concentrated by rotary evaporator under high vacuum. The residual oil is purified by flash chromatography on silica gel (3:1 hexanes/EtOAc) to give 7-fluoro-2-nitronaphthalene as a dark red solid.

Workup

  1. concentrationthe reaction mixture is concentrated by rotary evaporator under high vacuum
  2. customThe residual oil is purified by flash chromatography on silica gel (3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-00452f2f90c640288769d270a3a68b97
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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