p-Fluoronitrobenzene → 1-(5-Fluoro-2-nitrobenzylsulfonyl)naphthalene

HRID 547258Notes

Reaction equation

HRID 547258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:12][S:13]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].CC([O-])(C)C.[K+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[CH2:12][S:13]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 593041751-(5-Fluoro-2-nitrobenzylsulfonyl)naphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A stirred solution of 4-fluoro-nitrobenzene (1 equiv.) and chloromethyl-1-naphthylsulfone (1 equiv.) in dry THF under nitrogen at −78° C., was treated with 1.0 M KOt-Bu (2.2 equiv., 1.0 M in THF), warmed to −20° C. over 1 h period, quenched with acetic acid and treated sequentially with water, saturated aqueous NaHCO3 and extracted with ether. The combined extracts were washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was chromatographed (Silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent) to give 1-(5-fluoro-2-nitrobenzyl-sulfonyl)naphthalene.

Workup

  1. customquenched with acetic acid
  2. additiontreated sequentially with water, saturated aqueous NaHCO3
  3. extractionextracted with ether
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed (Silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent)

Sources & evidence

ORD record
ord-c1ebed1c900a45ffb59f1bd8aadd09b2
Source dataset
uspto-grants-2011_05
Patent number
US07939520B2

Reaction notes

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