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

HRID 1736498Notes

Reaction equation

HRID 1736498 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=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

Procedure

A solution of 5-bromo-2-methoxyphenol (74 g), cyclopentyl bromide (80.5 g) and potassium carbonate (73.6 g) in dimethylformamide (500 mL) is stirred at 60° C. for 16 hours. It is then concentrated and the resulting residue is treated with water (250 mL). This mixture is then extracted with dichloromethane (3×250 mL) and the combined extracts are dried over magnesium sulphate, and evaporated, to give 4-bromo-2-cyclopentyloxyanisole (95.5 g) in the form of a pale brown liquid. [NMR (CDCl3): 1.56-1.68 (m,2H), 1.77-1.99 (m,6H), 3.81 (s,3H), 4.71-4.75 (m,1H), 6.72 (d,1H), 6.98 (d,1H), 7.00 (dd,1H)].

Workup

  1. concentrationIt is then concentrated
  2. additionthe resulting residue is treated with water (250 mL)
  3. extractionThis mixture is then extracted with dichloromethane (3×250 mL)
  4. dry with materialthe combined extracts are dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e4411e39027645b3ab60d01af1558bd2
Source dataset
uspto-grants-1996_07
Patent number
US05541219

Reaction notes

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