Bromocyclopentane → HCID 21187828, compound

HRID 356973Notes

Reaction equation

HRID 356973 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([OH:10])[CH:3]=1.[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 211879495-Bromo-2-(methylsulfanyl)phenol

Product 1

HCID 21187828HCID 21187828, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 4-bromo-2-hydroxythioanisole (15.9 g) and cyclopentyl bromide (16.05 g) in dry dimethylformamide (170 mL) is treated with anhydrous potassium carbonate (14.7 g) and the mixture is heated at 60° C. for 1 day. After cooling, the solution is diluted with water (250 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are dried over magnesium sulfate and concentrated. The residue is subjected to flash chromatography, eluting with a mixture of ethyl acetate and pentane (5:95 v/v), to give 4-bromo-2-cyclopentyloxy-1-(methylthio)benzene, in the form of an oil (17.2 g). [NMR (DMSO): 7.14-7.03(m,3H),4.93(m,1 H), 2.33(s,3H),2.0-1.53(m,8H)].

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined extracts are dried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluting with a mixture of ethyl acetate and pentane (5:95 v/v)

Sources & evidence

ORD record
ord-d32f4bcf780e48939ea1828df10a1ac2
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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