Dinitrofluorobenzene → Bis(2,4-dinitrophenyl) ether

HRID 1614359Notes

Reaction equation

[H-].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1F)([O-:5])=[O:4].[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[O:19][C:20]1[CH:16]=[CH:17][C:18]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N+:3]([O-:5])=[O:4])([O-:5])=[O:4]

Participants

Reactant 3

HCID 6264Dinitrofluorobenzene

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

Product 1

HCID 95146Bis(2,4-dinitrophenyl) ether

Procedure

This compound was made by the procedure of Example 2 from Compound A (46.5 g, 0.010 mole), NaH (4 g as 60% oil suspension, 0.10 mole) and 2,4-dinitrofluorobenzene (27.9 g, 0.15 mole) in THF (150 ml). The final product was purified by distillation to give a liquid product, yield 45.0 g (71.3%). Bp. 150°-160° C./0.5 mm. H1NMR (CDCl3): δ8.80 (d, J=2.5 Hz, 1H), 8.70 (dd, J=2.5, 10 Hz, 1H), 7.24 (d, J=10 Hz, 1H), 4.68 (t, J=12 Hz, 2H); F19NMR (CDCl3): -71.3 (d, J=10.1 Hz, 2F), -77.4 (m, 1F), -80.2 (q, J=7.6 Hz, 3F), -82.5 to -86.0 (m, 4F), -122.9 (t, J=11.6 Hz, 2F), -145.9 (q, J=19.4 Hz, 1F).

Workup

distillationThe final product was purified by distillation
customto give a liquid product, yield 45.0 g (71.3%)

Sources & evidence

ORD record: ord-2ade62146abc4870b35c1b0169eb8b8d
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196569

Reaction notes

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