2-Chloro-1-fluoro-4-nitrobenzene → Tert-butyl-(2-(2-chloro-4-nitrophenoxy)ethoxy)dimethylsilane

HRID 633443Notes

Reaction equation

HRID 633443 reaction equation
CC(C)([O-])C.[K+].[Si:7]([O:14][CH2:15][CH2:16][OH:17])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Cl:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1F>C1COCC1>[C:10]([Si:7]([O:14][CH2:15][CH2:16][O:17][C:24]1[CH:23]=[CH:22][C:21]([N+:26]([O-:28])=[O:27])=[CH:20][C:19]=1[Cl:18])([CH3:9])[CH3:8])([CH3:12])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 86704535Tert-butyl-(2-(2-chloro-4-nitrophenoxy)ethoxy)dimethylsilaneYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (354 mg, 3.2 mmol) was added in one portion to a stirred solution of 2-((tert-butyldimethylsilyl)oxy)ethan-1-ol (506 mg, 2.9 mmol) in THF (3 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 30 min then 3-chloro-4-fluoronitrobenzene (251 mg, 1.4 mmol) was added in one portion (reaction turned dark color). The mixture was stirred at 0° C. for 10 min then the ice-bath removed, the reaction was allowed to warm to room temperature (10 min) and stirred for 1 hr. The solvent was removed under vacuum and the residue partitioned between EtOAc (50 mL) and H2O (50 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic layers dried (Na2SO4), filtered and the solvent removed under vacuum to leave the product as an oil (yield assumed quantitative=475 mg). The product was used in the next step without further purification.

Workup

  1. stirringThe mixture was stirred at 0° C. for 10 min
  2. customthe ice-bath removed
  3. temperatureto warm to room temperature (10 min)
  4. stirringstirred for 1 hr
  5. customThe solvent was removed under vacuum
  6. customthe residue partitioned between EtOAc (50 mL) and H2O (50 mL)
  7. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  8. dry with materialthe combined organic layers dried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-13f6bba4fa4245db89d1b9e5db7e4796
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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