[ CAS No. 253429-31-1 ]

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2D
Chemical Structure| 253429-31-1
Chemical Structure| 253429-31-1
Structure of 253429-31-1

Quality Control of [ 253429-31-1 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 253429-31-1 ]

SDS

Product Details of [ 253429-31-1 ]

CAS No. :253429-31-1MDL No. :MFCD09056781
Formula :C8H4BrFOBoiling Point :232.617°C at 760 mmHg
Linear Structure Formula :-InChI Key :IYRKPHRAECMQTJ-UHFFFAOYSA-N
M.W :215.02Pubchem ID :22144769
Synonyms :

Computed Properties of [ 253429-31-1 ]

TPSA : 13.1 H-Bond Acceptor Count : 2
XLogP3 : 3.1 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 253429-31-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 253429-31-1 ]

  • Upstream synthesis route of [ 253429-31-1 ]
  • Downstream synthetic route of [ 253429-31-1 ]

[ 253429-31-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 253429-18-4 ]
  • [ 253429-31-1 ]
YieldReaction ConditionsOperation in experiment
51% With polyphosphoric acid In toluene for 5.00 h; Reflux A solution of 2-Bromo-5-fluorophenol (228.00 g, 1.19 mol), Potassium carbonate (247.47 g, 1.79 mol) in N,N-Dimethylformamide (3.00 L) was treated with 2-Bromo-1,1-diethoxyethane (197.54 mL, 1.31 mol) and heated at 135 °C for 7 h. The reaction mixture was concentrated in vacuo and extracted with EtOAc (3 * 2 L). The combined organic layers were washed with aq NaOH (2 M, 4 L). The organic layer was dried (MgSO4), filtered, concentrated in vacuo to yield 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (362.00 g; Yield = 98percent) that was used as it is in the next step. 1H NMR (400 MHz, D6-DMSO) δ 7.58 (d, 1H, J = 6.8 & 8.8 Hz), 7.11 (dd, 1H, J = 2.8 & 10.8 Hz), 6.76 (dt, 1H, J = 2.2 & 8.1 Hz), 4.81 (t, 1H, J = 5.1 Hz), 4.03 (d, 2H, J = 5.1 Hz), 3.73-3.56 (m, 4H), 1.13 (t, 6H, J = 6.6 Hz). A solution of 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (352.00 g, 1.15 mol) in toluene (2500 mL, 2.3 mol) was treated with polyphosphoric acid (370.00 g, 3.4 mol) and heated at reflux for 5 h. The reaction mixture was concentrated in vacuo diluted with water (3 L) and the extracted with EtOAc (4 L). The organic layer was washed with aq NaOH (2 L), filtered, concentrated in vacuo and purified by distillation at reduced pressure to yield (4) 7-bromo-4-fluorobenzofuran (125.00 g; Yield = 51percent. bp 80 °C (1 mm/Hg) as a colorless liquid which solidified at rt. 1H NMR (400 MHz, CDCl3) δ 7.67 (d, 1H, J = 2.2 Hz), 7.39 (dd, 1H J = 5.1 & 3.7 Hz), 6.94 (d, 1H, J = 2.2 Hz), 6.86 (t, 1H, J = 8.8 Hz).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 447 - 458
  • 2
  • [ 664364-73-2 ]
  • [ 253429-31-1 ]
Reference: [1] Patent: EP1553074, 2005, A1. Location in patent: Page/Page column 47
  • 3
  • [ 147460-41-1 ]
  • [ 253429-31-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 447 - 458
[2] Patent: WO2008/82484, 2008, A1
[3] Patent: CN108658908, 2018, A
  • 4
  • [ 2032-35-1 ]
  • [ 147460-41-1 ]
  • [ 253429-31-1 ]
Reference: [1] Synlett, 2004, # 8, p. 1351 - 1354
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