7-Chloro-5-(4-methoxy-benzyloxy)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one → 7-Chloro-5-hydroxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427541Notes

Reaction equation

HRID 2427541 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:24]CC2C=CC(OC)=CC=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2>FC(F)(F)C(O)=O.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:24])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:15][CH:14]=1)[CH2:7]2

Participants

4

Reactant 1

HCID 579494297-Chloro-5-(4-methoxy-benzyloxy)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Product 1

HCID 579497007-Chloro-5-hydroxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

7-Chloro-5-(4-methoxy-benzyloxy)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (5.0 mg) was dissolved in a 1:1 mixture of trifluoroacetic acid and dichloromethane. The reaction was stirred over the weekend. The mixture was then washed with water, brine, dried over sodium sulfate, filtered and concentrated to provide the title compound (1.87 mg). 1H NMR (300 MHz, CDCl3): δ 7.36 (d, 2H), 7.20 (d, 2H), 6.94 (s, 1H), 6.76 (s, 1H), 4.76 (s, 2H), 4.19 (s, 2H).

Workup

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-61ed459b6b1d40c99aa02ff0c057f02c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…