Ethanol → 6-Fluoro-[1,1';4'1'']terphenyl-3,4-diamine

HRID 1945313Notes

Reaction equation

CCO.O.[F:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.[NH4+].[Cl-]>CCOC(C)=O.[Fe]>[F:5][C:6]1[C:7]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:8][C:9]([NH2:13])=[C:10]([NH2:12])[CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of EtOH (40 mL, H2O (10 mL) and 3 (663 mg, 2.1 mmol) was added Iron (889 mg, 16 mmol) and NH4Cl (562 mg, 10.5 mmol). The resulting suspension was allowed to stir for 18 h at 50° C. The crude suspension was diluted with copious amounts of EtOAc and filtered over a pad of Celite. The resulting yellow solution was concentrated in vacuo then purified on ISCO (EtOAc/Hexanes=7/3) to give title compound 4.

Workup

filtrationfiltered over a pad of Celite
concentrationThe resulting yellow solution was concentrated in vacuo
customthen purified on ISCO (EtOAc/Hexanes=7/3)

Sources & evidence

ORD record: ord-974228079ccc4c279825a9b9d6ea193b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394969B2

Reaction notes

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