Water → 1-(Cyclopentyloxy)-2-iodobenzene

HRID 1034388

Reaction equation

HRID 1034388 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[Br-].Br[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.O>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 962WaterHCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 199598491-Bromocyclopentane bromide

Product 1

HCID 153433181-(Cyclopentyloxy)-2-iodobenzeneYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-iodophenol (8.0 g, 36.4 mmol), milled potassium carbonate (5.5 g, 39.9 mmol, 1.1 eq) and 1-bromocyclopentane bromide (3.9 ml, 36.4 mmol) in 25 ml of N,N-dimethylformamide was heated at 120° C. for 1.1 hrs and cooled. The mixture was poured into water and extracted twice with ether. The ether layer was dried over magnesium sulfate, filtered, and concentrated to give an oil. The crude product was dissolved in ethyl acetate and filtered through a short pad of silica gel. The filtrate was redried over magnesium sulfate, filtered and concentrated under vacuum to give 10 g (95%) of product as an oil.

Workup

  1. temperaturecooled
  2. extractionextracted twice with ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. filtrationfiltered through a short pad of silica gel
  8. dry with materialThe filtrate was redried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2ea6a40080064913bfc2731412cc17c2
Source dataset
uspto-grants-1994_05
Patent number
US05316755

Linked notes

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