Bromocyclopentane → 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

HRID 2379578Notes

Reaction equation

HRID 2379578 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH:17]1(Br)[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O.C1(Br)CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:7]=1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium Carbonate3×HCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzeneYield 73,268.102%

Reagents, catalysts & solvents 2

HCID 8728BromocyclopentaneCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution 5-Bromo-2-methoxyphenol (30.6 g, 0.15 mmol) (preparation 3) in N, N-dimethylformamide (130 ml) under an argon atmosphere was added potassium carbonate (23.0 g, 0 . 17tool) and cyclopentyl bromide (18 ml, 0.18 mol). The resulting mixture was heated at 90° C. for 20 hr., at which time additional potassium carbonate (5.6 g, 0.04 mol) and cyclopentyl bromide (3 ml, 0.03 mmol) were added. Heating was resumed for 8 hr and additional potassium carbonate (5.6 g, 0.04 mol) and cyclopentyl bromide (3 ml, 0.03 mmol) were added. After heating at 90° C. for an additional 16 hr, the reaction mixture was allowed to cool and was concentrated under reduced pressure. The residue was partitioned between ether and water. The organic extract was washed with water (three times) and dried (magnesium sulfate). The solvate was removed in vacuo and the residue was purified by flash chromatography, eluting with 3% ether/hexanes to provide a pale yellow oil (29.8 g, 73%).

Workup

  1. temperatureHeating
  2. temperatureAfter heating at 90° C. for an additional 16 hr
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was partitioned between ether and water
  6. extractionThe organic extract
  7. washwas washed with water (three times)
  8. dry with materialdried (magnesium sulfate)
  9. customThe solvate was removed in vacuo
  10. customthe residue was purified by flash chromatography
  11. washeluting with 3% ether/hexanes

Sources & evidence

ORD record
ord-66b1311818f44b0fba688021faf4797a
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

Loading…