1,2-Difluorobenzene → HCID 21905880, compound

HRID 1581710Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])CCC.[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2=[O:25]>CCOCC.CCCCCC.C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[F:8])[OH:25]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 5.6 g of 1,2-difluorobenzene in 50 ml of ether is cooled to −10° C., 31 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise and the mixture is stirred at −10° C. for 2 hours. The reaction mixture is cooled to −50° C., a solution of 4 g of 5-chloro-1H-indole-2,3-dione in 40 ml of THF is added and the resulting mixture is stirred for 12 hours, while allowing the temperature to return to RT. The reaction mixture is poured into a concentrated HCl/ice/water mixture, the resulting mixture is extracted with EtOAc, the organic phase is washed with 1N NaOH solution, with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 2.8 g of the expected product are obtained after crystallization from iso-ether; m.p.=248° C.

Workup

temperatureThe reaction mixture is cooled to −50° C.
stirringthe resulting mixture is stirred for 12 hours
customto return to RT
extractionthe resulting mixture is extracted with EtOAc
washthe organic phase is washed with 1N NaOH solution, with water
dry with materialdried over Na2SO4
customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record: ord-3d80645627464ec4b963939ef26802cc
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730695B2

Reaction notes

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