1,3-Dibromopropane → 5-(3-Bromo-propoxy)-6-methoxy-indan-1-one

HRID 460342Notes

Reaction equation

HRID 460342 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.[Br:14][CH2:15][CH2:16][CH2:17]Br.[H-].[Na+]>CN(C=O)C>[Br:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one2×

Product 1

HCID 184456765-(3-Bromo-propoxy)-6-methoxy-indan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-Hydroxy-6-methoxy-indan-1-one (Intermediate H) (5.0 g, 0.028 mole), 1,3-dibromopropane (5.7 mL, 0.056 mole) and sodium hydride (1.2 g, 0.028 mole) were stirred in 50 mL of DMF at room temperature overnight under Argon. The reaction mixture was quenched with water (150 mL), extracted with ethyl acetate, then washed with 1N HCl and brine. The extract was dried over sodium sulfate and the solvent removed in vacuo to yield the title compound, 5-(3-Bromo-propoxy)-6-methoxy-indan-1-one. MS m/z 297 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water (150 mL)
  2. extractionextracted with ethyl acetate
  3. washwashed with 1N HCl and brine
  4. dry with materialThe extract was dried over sodium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-623b44e6fa98417db08752f5269dea30
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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