Nitric Acid → (2,3-Difluoro-5-nitrophenyl)acetic acid

HRID 2114873Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

Conditions

Temperature: -10 °C

Procedure

2,3-Difluoro-phenyl)-acetic acid (11, 5 g, 0.0290 mol) is dissolved in concentrated sulfuric acid (20 ml) and the resulting solution cooled to −10° C. with vigorous stirring. A solution of nitric acid (1.88 ml, 69.3%, 0.0290 mol) and sulfuric acid (2 ml) is added dropwise at a rate such that the temperature remains below −5° C. The thickened slurry is stirred for 15 minutes and then poured on ice. The resulting precipitate is filtered and dried under vacuum (6.3 g, 99%) and consists of a 50/50 mixture of 5 and 6-NO2 regioisomers suitable for use directly in the next step.

Workup

customremains below −5° C
additionpoured on ice
filtrationThe resulting precipitate is filtered
customdried under vacuum (6.3 g, 99%)
additionconsists of a 50/50 mixture of 5 and 6-NO2 regioisomers suitable for use directly in the next step

Sources & evidence

ORD record: ord-9cbe523e02934e7c8c1d1e03ec3f1a83
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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