2,4-Difluoronitrobenzene → HCID 58421530, compound

HRID 406024Notes

Reaction equation

HRID 406024 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C@@H:12]1([OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[OH:18].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([O:18][C@@H:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C@@H:12]2[OH:19])[CH:7]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 92903rel-(1R,2S)-1,2-CyclohexanediolHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 58421530HCID 58421530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,4-Difluoronitrobenzene (0.549 ml) and cis-1,2-cyclohexanediol (0.581 g) in THF (10.0 ml), cooled with an ice-bath, was added lithium bis(trimethylsilyl)amide (1 mol/1 solution in THF; 5.00 ml). The mixture was stirred overnight at rt, and then evaporated to dryness. The residue was taken up in ethyl acetate, extracted once with hydrochloric acid (1 mol/l) and twice with NaOH solution (1 mol/l), dried with magnesium sulphate, filtered and evaporated to dryness. The residue was purified by column chromatography (silica; methylene chloride/methanol 100:0=>97:3) to yield a yellowish oil.

Workup

  1. customevaporated to dryness
  2. extractionextracted once with hydrochloric acid (1 mol/l) and twice with NaOH solution (1 mol/l)
  3. dry with materialdried with magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography (silica; methylene chloride/methanol 100:0=>97:3)
  7. customto yield a yellowish oil

Sources & evidence

ORD record
ord-83e4e04e66fa4ebbb0bb3bbe42295b84
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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