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Chemical Structure| 148378-71-6 Chemical Structure| 148378-71-6

Structure of 148378-71-6

Chemical Structure| 148378-71-6

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Product Details of [ 148378-71-6 ]

CAS No. :148378-71-6
Formula : C10H8Br2O
M.W : 303.98
SMILES Code : O=C1C(Br)CCC2=C1C=C(Br)C=C2
MDL No. :MFCD26521751

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Application In Synthesis of [ 148378-71-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 148378-71-6 ]

[ 148378-71-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 148378-71-6 ]
  • [ 345995-25-7 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
27.3% With lithium chloride; In DMF (N,N-dimethyl-formamide); at 155℃; for 0.5h;Heating / reflux; of 5-Bromo-1-naphthalenol. [0096] The crude mixture of 2,5-dibromo-1-tetralone (16.08 g, 52.9 mmol,), LiCl (5.61 g, 132 mmol), and 120 mL of dry DMF were combined under an N2 atmosphere and heated to reflux (155° C.). The mixture turned dark brown. HPLC showed complete consumption of the starting material in just 0.5 h. After cooling to room temperature, the mixture was diluted with 1 N HCl (200 mL) and extracted three times with Et2O (100 mL, 25 mL, 25 mL). The Et2O layers were combined to give a brown hazy mixture (some emulsion). After stirring with decolorizing carbon (10 g, Calgon ADP) and filtration through hyflo supercel, a clear light yellow solution was obtained. This solution was extracted with 3 N NaOH (100 mL, 25 mL), leaving the non-naphtholic byproducts behind. The brown NaOH extracts were combined, acidified to pH 1 with conc. HCl, and extracted with CH2Cl2 (100 mL, 25 mL). The combined CH2Cl2 layers formed a deep red solution. After stirring with decolorizing carbon (5 g, Darco G-60) and filtration through hyflo supercel, the solution was again light yellow. An equal volume of heptane was added, and the CH2Cl2 was distilled away. When the temperature reached 75° C., gray precipitate became evident. This increased substantially on cooling to room temperature. Following filtration and drying in vacuo at 50° C., a product mixture of gray solid (5.92 g, 50.2percent) was obtained. HPLC showed this to be a mixture of 7-bromo-1-naphthol (48.3percent) and 5-bromo-1-naphthol (50.8percent). However, 1H NMR (CDCl3) integration showed that the actual ratio was about 9/1 5-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
  • 2
  • [ 148378-71-6 ]
  • [ 91270-69-8 ]
 

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