HCID 58566301, compound → HCID 58566716, compound

HRID 1876371Notes

Reaction equation

HRID 1876371 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][C:10]2[CH2:14][CH2:13][CH2:12][CH:11]=2)[C:3]=1[OH:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[O:15][C:10]3([CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:9][C:4]=2[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 58566301HCID 58566301, compound

Product 1

HCID 58566716HCID 58566716, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 2-bromo-4-chloro-6-(cyclopentenylmethyl)phenol (518) (5.7 g, 19.8 mmol) and Amberlyst® 15 ion-exchange resin (5.2 g) in toluene (100 mL) was heated at 80° C. for 3 hours. Subsequently, the Amberlyst 15 resin was filtered off and the filtrate was concentrated in vacuo to give 7-bromo-5-chloro-3H-spiro[benzofuran-2,1′-cyclopentane] (519) (5.4 g, 94.9%) as a yellow oil.

Workup

  1. filtrationSubsequently, the Amberlyst 15 resin was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-80edd25413f24daa9cccfdca480dc665
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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