Sodium Hydroxide → 2,3-Difluoro-1,4-di(2-thienyl)-5,6-diamino-benzene

HRID 1424309Notes

Reaction equation

HRID 1424309 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:5]([N+:14]([O-])=O)=[C:4]([N+:17]([O-])=O)[C:3]=1[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1.[OH-].[Na+]>[Fe].C(O)(=O)C>[F:8][C:7]1[C:2]([F:1])=[C:3]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[C:4]([NH2:17])=[C:5]([NH2:14])[C:6]=1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866706752,3-Difluoro-1,4-di(2-thienyl)-5,6-dinitro-benzene

Product 1

HCID 866706742,3-Difluoro-1,4-di(2-thienyl)-5,6-diamino-benzeneYield 84%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

2,3-difluoro-1,4-di(2-thienyl)-5,6-dinitro-benzene (3.0 g, 8.15 mmol), iron powder (5.5 g, 98 mmol) and acetic acid (100 ml) were stirred at 45° C. for 4 h. Then the mixture was poured into cold 5% NaOH solution (250 ml) and extracted with diethyl ether three times. The ether phase was washed with NaHCO3 solution, dried over MgSO4 and concentrated. Purification with column chromatograph afforded 2,3-difluoro-1,4-di(2-thienyl)-5,6-diamino-benzene as yellow powder (2.1 g, 84%). 1H and 19F NMR spectra were as expected.

Workup

  1. extractionextracted with diethyl ether three times
  2. washThe ether phase was washed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification with column chromatograph

Sources & evidence

ORD record
ord-ed7dca6246394d589107f3be1c6a5e71
Source dataset
uspto-grants-2015_01
Patent number
US08927684B2

Reaction notes

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