Water → HCID 60075148, compound

HRID 496420Notes

Reaction equation

HRID 496420 reaction equation
[CH3:1][O:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.B(Br)(Br)Br.[OH2:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:5][CH:6]=2)=[CH:4][C:3]([O:2][CH3:1])=[O:18])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 110951552-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 60075148HCID 60075148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.39 g (0.0451 mol) of the methoxy tetralone from step 7 in 250 mL CH2Cl2 is cooled in ice and treated dropwise with 29 mL of BBr3. The purple solution is kept at 0° for 0.5 hour, then at room temperature overnight. The solution is poured into H2O and extracted twice with Et2O. The Et2O is washed twice with 5% NaOH and the NaOH back extracted with Et2O. The NaOH extract is acidified with dil. HCl and extracted twice with Et2O. The Et2O is washed with sat. NaCl, dried over Mg SO4, and the solvent removed leaving 10.82 g of a brown foam. Chromatography on silica gel, eluting with CHCl3/MeOH (98:2) gives 2.05 g (19.1% yield) of the product as a pink solid. The structure is confirmed by NMR and mass spectroscopy.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted twice with Et2O
  4. washThe Et2O is washed twice with 5% NaOH
  5. extractionthe NaOH back extracted with Et2O
  6. extractionThe NaOH extract
  7. extractionextracted twice with Et2O
  8. washThe Et2O is washed with sat. NaCl
  9. dry with materialdried over Mg SO4
  10. customthe solvent removed

Sources & evidence

ORD record
ord-74550fb5deb14f45b54e139e58b994f2
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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