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[ CAS No. 52927-23-8 ]

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Chemical Structure| 52927-23-8
Chemical Structure| 52927-23-8
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Product Details of [ 52927-23-8 ]

CAS No. :52927-23-8 MDL No. :MFCD02179789
Formula : C10H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :223.07 g/mol Pubchem ID :12336394
Synonyms :

Safety of [ 52927-23-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52927-23-8 ]

  • Upstream synthesis route of [ 52927-23-8 ]
  • Downstream synthetic route of [ 52927-23-8 ]

[ 52927-23-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 345995-25-7 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
27.3% With lithium chloride In DMF (N,N-dimethyl-formamide) for 0.5 h; Heating / reflux 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).
27.3%
Stage #1: With lithium chloride In DMF (N,N-dimethyl-formamide) at 155℃; for 0.5 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 20℃;
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 9/15-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
Reference: [1] Patent: US2003/232833, 2003, A1, . Location in patent: Page 13
[2] Patent: US2003/225281, 2003, A1, . Location in patent: Page 12
  • 2
  • [ 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 0.5 h; 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).
Reference: [1] Patent: US2004/6229, 2004, A1, . Location in patent: Page/Page column 14
  • 3
  • [ 136131-50-5 ]
  • [ 52927-23-8 ]
  • [ 62456-32-0 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6704 - 6708
  • 4
  • [ 108-36-1 ]
  • [ 52927-23-8 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6704 - 6708
  • 5
  • [ 41498-06-0 ]
  • [ 52927-23-8 ]
Reference: [1] Synthesis, 1989, # 3, p. 167 - 172
  • 6
  • [ 68449-30-9 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
Reference: [1] Patent: US2003/225281, 2003, A1,
  • 7
  • [ 529-34-0 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
Reference: [1] Patent: US2003/225281, 2003, A1,
  • 8
  • [ 86-57-7 ]
  • [ 52927-23-8 ]
Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
  • 9
  • [ 5328-76-7 ]
  • [ 52927-23-8 ]
Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
  • 10
  • [ 103030-24-6 ]
  • [ 52927-23-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
  • 11
  • [ 4766-33-0 ]
  • [ 52927-23-8 ]
Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
  • 12
  • [ 136131-50-5 ]
  • [ 52927-23-8 ]
  • [ 62456-32-0 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6704 - 6708
  • 13
  • [ 345995-25-7 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
27.3% With lithium chloride In DMF (N,N-dimethyl-formamide) for 0.5 h; Heating / reflux 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).
27.3%
Stage #1: With lithium chloride In DMF (N,N-dimethyl-formamide) at 155℃; for 0.5 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 20℃;
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 9/15-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
Reference: [1] Patent: US2003/232833, 2003, A1, . Location in patent: Page 13
[2] Patent: US2003/225281, 2003, A1, . Location in patent: Page 12
  • 14
  • [ 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 0.5 h; 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).
Reference: [1] Patent: US2004/6229, 2004, A1, . Location in patent: Page/Page column 14
  • 15
  • [ 68449-30-9 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
Reference: [1] Patent: US2003/225281, 2003, A1,
  • 16
  • [ 529-34-0 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
Reference: [1] Patent: US2003/225281, 2003, A1,
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