Dichloromethane → HCID 21107221, compound

HRID 1765771Notes

Reaction equation

HRID 1765771 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12]C)[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 21107223HCID 21107223, compound

Product 1

HCID 21107221HCID 21107221, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred, cooled (ice bath) solution of 6-bromo-8-methoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate-64, 0.24 g, 0.83 mmol) in anhydrous-dichloromethane (4 mL) was treated with aluminum chloride (0.4 g, 3 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. It was poured into water and extracted with dichloromethane and ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a brown oil that was subjected to flash column chromatography over silica gel (230–400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title product as a pale yellow solid (0.13 g, 56%).

Workup

  1. extractionextracted with dichloromethane and ethyl acetate
  2. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a brown oil that

Sources & evidence

ORD record
ord-ab3bcd8a7ce44a56a11782d5378bd1cf
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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