1-Fluoro-2-nitrobenzene → 3,4-difluoro-N-(2-nitrophenyl)aniline

HRID 1818833Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C([Li])CCC.F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH:5][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3,4-difluoroaniline (10.0 mL, 1.0 mol) in tetrahydrofuran (200 mL) was cooled to −78° C., treated with n-butyllithium solution (44 mL of a 2.5 M hexanes solution, 1.1 mol), stirred at −78° C. for 1 h and then warmed to 0° C. for 30 min. The reaction mixture was cooled to −78° C. and 1-fluoro-2-nitrobenzene (9.5 mL, 0.9 mol) in tetrahydrofuran (10 mL) was slowly added and the reaction, after which the reaction was warmed to room temperature. The reaction mixture was evaporated to provide 3,4-difluoro-N-(2-nitrophenyl)aniline (22.76 g, 91%) as a brown solid. The crude product was taken on to the next step.

Workup

temperaturewarmed to 0° C. for 30 min
temperatureThe reaction mixture was cooled to −78° C.
customthe reaction
temperatureafter which the reaction was warmed to room temperature
customThe reaction mixture was evaporated

Sources & evidence

ORD record: ord-9a654d86d53e4deaab660f060a207f0a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601722B2

Reaction notes

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