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Cesium carbonate → 4-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-2-hydroxy-benzoic acid methyl ester

HRID 1392276
Notes
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Reaction equation

HRID 1392276 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].Br[CH2:14][CH2:15][CH2:16][O:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH2:15][CH2:16][O:17][N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])=[CH:6][C:5]=1[OH:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 2655692-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 691957184-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-2-hydroxy-benzoic acid methyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 180Acetone
Solvent

Procedure

To a solution of 2,4-dihydroxy-benzoic acid methyl ester (1.42 g, 8.45 mmol) and 2-(3-bromo-propoxy)-isoindole-1,3-dione (2.00 g, 7.04 mmol) ) in acetone (50 mL) was added cesium carbonate (6.88 g, 21.1 mmol). The mixture was heated to reflux for 3 hours and allowed to cool back to room temperature. The mixture was partitioned between ethyl acetate and brine and the layers were then separated. The aqueous layer was extracted with two additional portions of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using chloroform to give 4-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-2-hydroxy-benzoic acid methyl ester (0.76 g, 30%) as a white solid. 1H NMR (400 MHz, CDCl3); δ 10.86 (s, 1H), 7.76 (m, 2H), 7.68 (m, 3H), 6.40 (m, 2H), 4.35 (t, 2H), 4.21 (t, 2H), 3.85 (s, 3H), 2.20 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe mixture was partitioned between ethyl acetate and brine
  4. customthe layers were then separated
  5. extractionThe aqueous layer was extracted with two additional portions of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-5bd36397283341b5a15f19ef794b4408
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342039B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes