Potassium Carbonate → Tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silane

HRID 1667769Notes

Reaction equation

HRID 1667769 reaction equation
[F:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:15][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:22]([Si:19]([O:18][CH2:17][CH2:16][CH2:15][O:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]=1[O:9][CH3:10])([CH3:20])[CH3:21])([CH3:24])([CH3:25])[CH3:23]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 67426546HCID 67426546, compound

Product 1

HCID 67428158Tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silaneYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.350 g (1.87 mmole) of 5-fluoro-2-methoxy-4-nitro-phenol, 0.568 g (2.25 mmole) of (3-bromo-propoxy)-tert-butyl-dimethyl-silane, 1.29 g (9.35 mmole) of potassium carbonate and 5 mL of dimethylformamide was heated at 60 degrees for 3 hours. The mixture was cooled, poured into 50 mL of dilute ammonium chloride solution and extracted three times with 25 mL of ethyl acetate. The combined organic extracts were washed three times with 25 mL of water, once with 25 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-hexanes (60:40) to give 0.469 g of tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silane (IV.42) as a white solid.

Workup

  1. temperaturewas heated at 60 degrees for 3 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted three times with 25 mL of ethyl acetate
  4. washThe combined organic extracts were washed three times with 25 mL of water
  5. dry with materialonce with 25 mL of brine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with dichloromethane-hexanes (60:40)

Sources & evidence

ORD record
ord-087fb06fdbae407490f4b9ec4d10671f
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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