Water → HCID 60611463, compound

HRID 1844403Notes

Reaction equation

HRID 1844403 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].Br[CH2:11][CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[O:9][CH2:11][CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 68992,6-DichlorophenolHCID 10796Cesium carbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 60611463HCID 60611463, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2,6-dichlorophenol (500 mg, 3.07 mmol), tetrabutyl ammonium iodide (227 mg, 0.613 mmol) and 2-(3-bromopropyl)isoindoline-1,3-dione (905 mg, 3.37 mmol) was stirred in THF (5 mL) at rt. Cs2CO3 (1.80 g, 5.52 mmol) was added. The resulting mixture was stirred at 50° C. for 16 h. H2O was added to the reaction mixture and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by triturating with Et2O to yield Intermediate 9A (1010 mg, 2.88 mmol, 94% yield) as a white powder. LC-MS (ESI) 365 (M+H), RT=2.23 min (Method B).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customby triturating with Et2O

Sources & evidence

ORD record
ord-2174d5bf7c7d4fa3859e64e103a65f76
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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