Boron tribromide → HCID 68459385, compound

HRID 502618Notes

Reaction equation

HRID 502618 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14]C)[C:10]([CH3:16])=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH:1]([C:4]1[C:13]([OH:14])=[CH:12][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:16])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68461893HCID 68461893, compound

Product 1

HCID 68459385HCID 68459385, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Isopropyl-7-methoxy-1-methyl-naphthalene (2.1 g, 9.79 mmol) was dissolved in 30 mL methylene chloride and the resulting solution was cooled in an ice bath. Boron tribromide (3.3 mL, 2.2 mmol in methylene chloride) was added dropwise, and the solution was stirred for one hour at 0° C. under nitrogen atmosphere, then for 18 hours at room temperature. The reaction mixture was poured into ice water and extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (8:1 hexanes/dichloromethane) on silica to yield 1.79 g of 3-isopropyl-8-methyl-naphthalen-2-ol as an oil.

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. waitfor 18 hours at room temperature
  3. extractionextracted with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (8:1 hexanes/dichloromethane) on silica

Sources & evidence

ORD record
ord-e7e030252db24c8894334ffd86972090
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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