Water → 5-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline-1,3-dione

HRID 853798Notes

Reaction equation

HRID 853798 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:5]2=[O:19].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[CH2:26]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:5][C:4]3[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=3)=[CH:14][CH:13]=1)[C:5]2=[O:19])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 197939855-Hydroxy-2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 694715505-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline-1,3-dioneYield 186%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 5-hydroxy-2-(4-hydroxyphenyl)isoindoline-1,3-dione (2.08 g) in DMF (20 mL) was added potassium carbonate (4.62 g) and a solution of benzyl bromide (3.07 g) in DMF (3.0 mL) dropwise under nitrogen atmosphere. The reaction was stirred at room temperature for 2 h then heated to 80° C. for 3 h. The mixture was cooled to room temperature, poured into water (250 mL) and let sit undisturbed for 2.0 h. The white solid was collected by filtration and washed with water. The solid was dried under high vacuum at 50° C. for 18 h yielding the title compound (3.30 g) as a white solid. 1H NMR (DMSO-d6): 7.87 (d, 1H, J=8.4 Hz), 7.48-7.35 (m, 12H), 7.32 (d, 2H, J=8.7 Hz), 7.13 (d, 2H, J=8.7 Hz), 5.35 (s, 2H), 5.17 (s, 2H); MS: 436 (MH+).

Workup

  1. temperaturethen heated to 80° C. for 3 h
  2. temperatureThe mixture was cooled to room temperature
  3. waitlet sit undisturbed for 2.0 h
  4. filtrationThe white solid was collected by filtration
  5. washwashed with water
  6. customThe solid was dried under high vacuum at 50° C. for 18 h

Sources & evidence

ORD record
ord-e63d17cc269a4f1fbad3885b5a44b3c6
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

Loading…