Bromochloromethane → 5,6-Methylenedioxy-1-tetralone

HRID 847264Notes

Reaction equation

HRID 847264 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-2b28ac7ff6384383ade68b3f401ce490
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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