2,4-Difluoronitrobenzene → HCID 58421665, compound

HRID 406007Notes

Reaction equation

HRID 406007 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:11]1[C:15]2([CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1.F[C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31]>C1COCC1>[F:29][C:27]1[CH:26]=[CH:25][C:24]([N+:30]([O-:32])=[O:31])=[C:23]([CH:28]=1)[O:21][CH:18]1[CH2:19][CH2:20][C:15]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 58421665HCID 58421665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

63 ml LiHMDS (1 M in THF) were added dropwise to a stirred solution of 10 g 1,4-dioxa-spiro[4.5]decan-8-ol in THF (60 ml) at 0° C. and the reaction stirred for 30 min. A solution of 2,4-difluor-1-nitro-benzene in THF (20 ml) was than added over 5 min and the reaction warmed to rt and stirred for 16 h. The reaction was quenched with sat. ammonium chloride solution and adjusted to pH 7 with 2N HCl. The solvent was removed under vacuum and the residue portioned between EtOAc (200 ml) and water (100 ml). The organic layer was separated and the aqueous phase washed with EtOAc (2×50 ml). The combined organic phases were washed with brine (50 ml) and separated. The organic phase was evaporated to give a solid that was used without further purification.

Workup

  1. additionthan added over 5 min
  2. stirringstirred for 16 h
  3. customThe reaction was quenched with sat. ammonium chloride solution
  4. customThe solvent was removed under vacuum
  5. customThe organic layer was separated
  6. washthe aqueous phase washed with EtOAc (2×50 ml)
  7. washThe combined organic phases were washed with brine (50 ml)
  8. customseparated
  9. customThe organic phase was evaporated
  10. customto give a solid that
  11. customwas used without further purification

Sources & evidence

ORD record
ord-9b74bb8e75fc41d99bbc9c1308c31034
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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