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Chemical Structure| 918793-01-8 Chemical Structure| 918793-01-8

Structure of 918793-01-8

Chemical Structure| 918793-01-8

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Product Details of [ 918793-01-8 ]

CAS No. :918793-01-8
Formula : C6H5BrFNO
M.W : 206.01
SMILES Code : OCC1=NC(Br)=CC=C1F
MDL No. :MFCD16607006

Safety of [ 918793-01-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Application In Synthesis of [ 918793-01-8 ]

* 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 [ 918793-01-8 ]

[ 918793-01-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 918793-01-8 ]
  • [ 31181-79-0 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogen;palladium over charcoal; In methanol; for 20h; Preparation 59; (3-Fluoro-pyridin-2-yl)-methanolDissolve (6-bromo-3-fluoro-pyridin-2-yl)-methanol (850 mg, 4.13 mmol) in methanol (40 mL) then purge the solution with nitrogen. Add palladium on carbon (200 mg of 5percent wet) and stir the mixture under a hydrogen atmosphere (2 balloons) for 20 h. Filter the mixture through Celite.(R). and wash the filter cake with methanol. Concentrate the filtrate under reduced pressure and dissolve the resulting residue in chloroform (150 mL). Wash the organics with saturated aqueous sodium bicarbonate (75 mL), dry over magnesium sulfate, filter, and concentrate to give 433 mg (82percent) of the title compound which is used without further purification. 1H NMR (300 MHz, CDCl3): delta 8.40 (m, IH), 7.42-7.36 (m, IH), 7.29-7.23 (m, IH), 4.84 (s, 2H), 3.97 (br s, IH); MS (APCI): m/z 110 [C6H6FNO - H2O + H]+.
  • 2
  • [ 918793-01-8 ]
  • [ 885267-36-7 ]
YieldReaction ConditionsOperation in experiment
69.4% With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 14h; To a solution of (6-bromo-3-fluoropyridin-2-yl)methanol (4 g, 19.42 mmol) in DCM (80 mL) cooled to 0 C was added Dess-Martin periodinane (12.35 g, 29.1 mmol). The mixture was warmed to room temperature and stirred for 14 h. The reaction mixture was quenched with saturated aqueous sodium bicarobonate (50 mL) and diluted with DCM (100 mL). The mixture was filtered through diatomaceous earth (Celite). The bed was washed with DCM (100 mL) and the filtrate was transferred to a separating funnel. The aqueous layer was discarded and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 6-bromo-3-fluoropicolinaldehyde (5.5 g, 27.0 mmol, 69.4 % yield) as a colorless oil. NMR (400 MHz, CDCh): delta 10.09 (s, 1H), 7.71 (dd, J= 8.8, 3.6 Hz, 1H), 7.50 - 7.46 (m, 1H).
  • 3
  • [ 885267-36-7 ]
  • [ 918793-01-8 ]
YieldReaction ConditionsOperation in experiment
90% With methanol; sodium tetrahydroborate; at 0 - 20℃; To a solution of <strong>[885267-36-7]6-bromo-3-fluoropicolinaldehyde</strong> (1.7 g, 8.33 mmol) in methanol (20 mL) at 0 C was added NaBH4 (0.473 g, 12.50 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure, diluted with water (10 mL) and extracted with ethyl acetate (2 x 50 mL). The ethyl acetate layer was washed with water (1 x 20 mL), saturated NaCl (1 x 20 mL), dried over Na2S04, filtered, and concentrated under reduced pressure to afford (6-bromo-3-fluoropyridin-2-yl)methanol (1.6 g, 7.53 mmol, 90% yield) was isolated as a brown solid. LCMS (ESI) m/e 205.9 (bromo pattern) [(M+H)+, calcd for CeHeBrFNO, 205.9]; LC/MS retention time (Method C): tR = 0.56 min.
With methanol; sodium tetrahydroborate; In tetrahydrofuran; for 0.5h; A solution of <strong>[885267-36-7]6-bromo-3-fluoropicolinaldehyde</strong> (250 mg, 1.226 mmol) in methanol (3 mL) and tetrahydrofuran (5 mL) was cooled to 0 C then sodium borohydride (46.4 mg, 1.226 mmol) was added in two portions. The reaction mixture was stirred for 30 mm. The reaction mixture was concentrated under reduced pressure. Water (15 mL) was added to the reaction mixture and the solution wasextracted with ethyl acetate (2 x 15 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford cmde (6-bromo-3-fluoropyridin-2- yl)methanol (236 mg, 1.100 mmol, 90% yield). LCMS (ESI) mle 206.0 (bromo pattern) [(M+H), calcd for C6H6BrFNO 205.91; LC/MS retention time (Method G)tR=1.l7mln.
 

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