O-Xylene → 1-Chloro-2-fluoro-3-nitrobenzene

HRID 2396435Notes

Reaction equation

[F-:1].CC(CC(O)CO)C.Cl[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C1(C)C(C)=CC=CC=1>>[Cl:17][C:16]1[C:11]([F:1])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=[CH:14][CH:15]=1

Participants

Reactant 4

HCID 7237O-Xylene

HCID 185552,3-Dichloronitrobenzene

HCID 28179Fluoride Ion

HCID 911714-Methylpentane-1,2-diol

Product 1

HCID 750161-Chloro-2-fluoro-3-nitrobenzene

Conditions

Temperature: 100 °C

Procedure

In a 1.5 liter flange flask and fitted with a distillation bridge and impeller stirrer, 279 g (4.8 tool) of fluoride, 218.5 g (0.3 mol) of trimethyl(ethoxypolyoxypropyl)ammonium chloride and 11.5 g (0.023 mol) of polyethylene glycol dimethyl ether 500 were introduced at 100° C. into the melt of 768 g (4 mol) of 2,3-dichloronitrobenzene. Subsequently, the mixture was azeotropically dried using 200 g (1.9 mol) of xylene and stirred for 24 hours at a temperature of 100° C. Amount of 3-chloro-2-fluoronitrobenzene formed: after 5 hours: 18 GC area-%. after 24 hours: 47 GC area-%.

Workup

customSubsequently, the mixture was azeotropically dried

Sources & evidence

ORD record: ord-93715521487843ad811ccacd4c35e9cc
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492875

Reaction notes

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