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

HRID 1383535Notes

Reaction equation

HRID 1383535 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>[CH:17]1([O:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[O:9][CH3:10])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzeneYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 5-bromo-2-methoxyphenol (74 g) and anhydrous potassium carbonate (73.6 g) in dry dimethylformamide (500 mL) is treated with cyclopentyl bromide (80.5 g) and the solution is heated at 60° C. for 16 hours. It is then concentrated, and the resulting residue is triturated with water (250 mL), and extracted with dichloromethane (3×250 mL). The combined extracts are dried and evaporated, to give 3-cyclopentyloxy-4-methoxyphenyl bromide (95.5 g), in the form of a light brown oil.

Workup

  1. concentrationIt is then concentrated
  2. customthe resulting residue is triturated with water (250 mL)
  3. extractionextracted with dichloromethane (3×250 mL)
  4. customThe combined extracts are dried
  5. customevaporated

Sources & evidence

ORD record
ord-e8df4b24b9ca4bf6bbb9723cc4804ec4
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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