p-Toluenesulfonic acid monohydrate → 2-(1-(4-Bromophenyl)-3-oxocyclobutyl)isoindoline-1,3-dione

HRID 222003Notes

Reaction equation

HRID 222003 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:11][C:10]3(OCC[O:12]3)[CH2:9]2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:9][C:10](=[O:12])[CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 582166062-(2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-yl)isoindoline-1,3-dione

Product 1

HCID 582165742-(1-(4-Bromophenyl)-3-oxocyclobutyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[2-(4-bromophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]-1H-isoindole-1,3(2H)-dione (7-2) (3.1 g, 7.48 mmol) and p-toluenesulfonic acid monohydrate (0.14 g, 0.75 mmol) in acetone (50 mL) was refluxed for 2 days. The cooled mixture was diluted with EtOAc, washed with sat. NaHCO3, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 0˜100% EtOAc in hexane, to give 2-[1-(4-bromophenyl)-3-oxocyclobutyl]-1H-isoindole-1,3(2H)-dione (7-3) as a colorless form.

Workup

  1. temperaturewas refluxed for 2 days
  2. washwashed with sat. NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0˜100% EtOAc in hexane

Sources & evidence

ORD record
ord-e527393a069f497aa6b7843f19e34b39
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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