Bromochloromethane → 5,6-Methylenedioxy-1-tetralone

HRID 653755Notes

Reaction equation

HRID 653755 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].[C:14](=O)([O-])[O-].[Cs+].[Cs+].BrCCl>CN(C=O)C>[CH2:14]1[O:12][C:11]2[C:2](=[C:3]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:13])[CH2:6][CH2:5][CH2:4]3)[O:1]1

Participants

5

Reactant 3

HCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 123536405,6-Dihydroxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 111168225,6-Methylenedioxy-1-tetraloneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the product of Example 177 (30 g) in DMF (390 ml) was added cesium carbonate (83 g) followed by bromochloromethane (33 g) and the resulting mixture heated to 100 ° C. and mechanically stirred for 2 hours. The reaction was cooled, filtered and the solids washed with ethyl acetate. The filtrate concentrated and the residue taken up into water and toluene. The layers were separate and the aqueous layer reextracted with toluene. The extracts were combined, dried (MgSO4), filtered, treated with charcoal, refiltered and concentrated to provide 29.9 g of the desired product, m.p. 132°-136° C.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washthe solids washed with ethyl acetate
  4. concentrationThe filtrate concentrated
  5. customThe layers were separate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. additiontreated with charcoal
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f907f18fe35547869774efd18a57776a
Source dataset
uspto-grants-1992_07
Patent number
US05128362

Reaction notes

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