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[ CAS No. 140472-69-1 ] {[proInfo.proName]}

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Chemical Structure| 140472-69-1
Chemical Structure| 140472-69-1
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Product Details of [ 140472-69-1 ]

CAS No. :140472-69-1 MDL No. :MFCD06797980
Formula : C7H5BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WGIBEMRBLBGETQ-UHFFFAOYSA-N
M.W : 217.02 Pubchem ID :15735511
Synonyms :

Safety of [ 140472-69-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P273-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 140472-69-1 ]

* 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.

  • Upstream synthesis route of [ 140472-69-1 ]
  • Downstream synthetic route of [ 140472-69-1 ]

[ 140472-69-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 188815-32-9 ]
  • [ 140472-69-1 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In water at 100℃; for 24 h; Step 1:
3-Bromo-5-hydroxy-benzoic acid
To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo-benzoic acid (20 g, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol).
The reaction mixture was heated at 100° C. for 24 h.
After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through Celite.(TM)..
The filtrate was then acidified with 10percent aq. HCl and extracted into ethyl acetate.
The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid (12.3 g, 93percent yield). HR-ES (-) calcd for C7HSO3Br [M-H]- 214.9349, observed 214.9350
93%
Stage #1: With sodium hydroxide In water at 100℃; for 24 h;
Stage #2: With hydrogenchloride In waterAcidic aqueous solution
To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo- benzoic acid (2Og, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol). The reaction mixture was heated at 100° C for 24 h. After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through Celite.(TM).. The filtrate was then acidified with 10percent aq. HCl and extracted into ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid (12.3g, 93percent yield). HRMS calcd for C7H5O3Br [M-H]" 214.9349, observed 214.9350
Reference: [1] Patent: US2010/240678, 2010, A1, . Location in patent: Page/Page column 22
[2] Patent: WO2009/77385, 2009, A1, . Location in patent: Page/Page column 63
[3] Patent: WO2005/113494, 2005, A2, . Location in patent: Page/Page column 118-119
  • 2
  • [ 42237-85-4 ]
  • [ 140472-69-1 ]
YieldReaction ConditionsOperation in experiment
66% for 1.75 h; Reflux The title compound of Preparation 50 (5.80 g, 26.85 mmols), in 10percent sulphuric acid (55 ml), was diazotised with sodium nitrite (1.85 g), and the solution boiled with dilute sulphuric acid (1:1) ( 30ml) for one hour and forty-five minutes. The solution was cooled at room temperature. The suspension was filtered and the solid give 3.83 g (66percent) of the title compound. HPLC/MS (10 min) retention time 5.06 min LRMS: m/z 215 (M-1)
66% With sulfuric acid; water; sodium nitrite In water for 1.75 h; Reflux PREPARATION 22
3-Bromo-5-hydroxybenzoic acid
The title compound of Preparation 21 (5.80 g, 26.85 mmols), in 10percent sulphuric acid (55 mL), was diazotised with sodium nitrite (1.85 g), and the solution boiled with dilute sulphuric acid (1:1) (30 mL) for one hour and forty-five minutes.
The solution was cooled at room temperature.
The suspension was filtered and the solid give 3.83 g (66percent) of the title compound.
HPLC/MS (10 min) retention time 5.06 min
LRMS: m/z 215 (M-1)
Reference: [1] Patent: EP2196465, 2010, A1, . Location in patent: Page/Page column 43
[2] Patent: EP2394998, 2011, A1, . Location in patent: Page/Page column 23
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
  • 3
  • [ 6307-83-1 ]
  • [ 140472-69-1 ]
Reference: [1] Patent: EP2394998, 2011, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
  • 4
  • [ 121-92-6 ]
  • [ 140472-69-1 ]
Reference: [1] Patent: EP2394998, 2011, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
  • 5
  • [ 140472-69-1 ]
  • [ 77-78-1 ]
  • [ 157893-14-6 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 461,464[2] Journal of the Chemical Society, 1959, p. 1027,1030
[3] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1518 - 1523
  • 6
  • [ 140472-69-1 ]
  • [ 199177-26-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3217 - 3227
[2] Patent: WO2014/60431, 2014, A1,
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 11, p. 2937 - 2957
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