1,2-Dichlorobenzene → 1-Fluoro-2-nitronaphthalene

HRID 2379460

Reaction equation

HRID 2379460 reaction equation
[F:1][B-](F)(F)F.N#[O+].N[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].ClC1C=CC=CC=1Cl>ClCCl>[F:1][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 1364032-Nitronaphthalen-1-amineHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 220084711-Fluoro-2-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred slurry of nitrosonium tetrafluoroborate (Aldrich) (10 % molar excess, (cf. David J. Milner, Synthetic Communications (1992) 22 (1), 73-82.)) in dichloromethane at 0° C. is added 1-amino-2-nitronaphthalene. After 30 minutes, ortho-dichlorobenzene is added and the dichloromethane is distilled off, and the dichlorobenzene is heated at 50°-200 ° C. to decompose the diazonium tetrafluoroborate. Removal of solvent and purification of the product by chromatography or crystallization yields 1-fluoro-2-nitronaphthalene.

Workup

  1. distillationthe dichloromethane is distilled off
  2. temperaturethe dichlorobenzene is heated at 50°-200 ° C.
  3. customRemoval of solvent and purification of the product
  4. customby chromatography or crystallization

Sources & evidence

ORD record
ord-d9497c760e6047559109574ac42038e4
Source dataset
uspto-grants-1994_11
Patent number
US05362747

Linked notes

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