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Chemical Structure| 41404-58-4 Chemical Structure| 41404-58-4
Chemical Structure| 41404-58-4

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CAS No.: 41404-58-4

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Product Details of 2-Bromo-5-fluoropyridine

CAS No. :41404-58-4
Formula : C5H3BrFN
M.W : 175.99
SMILES Code : C1=C(C=NC(=C1)Br)F
MDL No. :MFCD00234011
InChI Key :UODINHBLNPPDPD-UHFFFAOYSA-N
Pubchem ID :2783171

Safety of 2-Bromo-5-fluoropyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Bromo-5-fluoropyridine

* 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 [ 41404-58-4 ]
  • Downstream synthetic route of [ 41404-58-4 ]

[ 41404-58-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 41404-58-4 ]
  • [ 68-12-2 ]
  • [ 802325-29-7 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With n-butyllithium In hexanes; toluene at -78℃; for 1.5 h;
Stage #2: at -78℃; for 2 h; 		Preparation 56; (5-Fluoro-pyridin-2-yl)-methanol EPO <DP n="164"/>Add butyllithium (10.9 mL, 27.22 mmol, 2.5 M solution in hexanes) to a- 78 0C solution of 2-bromo-5-fluoro-pyridine (3.99 g, 22.68 mmol) in toluene (200 mL). Stir the reaction at -78 0C for 90 min and then add iV.iV-dimethylforrnamide (2.3 mL, 29.71 mmol) via syringe. Stir the reaction for an additional 2 h at -78 0C and then add sodium borohydride (1.72 g, 45.36 mmol) and allow the reaction to warm to room temperature over a 12 h period. Quench the reaction with saturated aqueous sodium bicarbonate (20 mL) and dilute with ethyl acetate (100 mL). Separate the organic phase and dry (magnesium sulfate), filter and concentrate in vacuo to give a yellow oil. Purify the oil by column chromatography (silica gel; 10percent to 50percent ethyl acetate in hexanes) to give 1.30 g (45percent) as a clear colorless oil. 1H NMR (300 MHz, CDCl3): δ 8.41s, IH), 7.46-7.37 (m, IH), 7.32-7.27 (m, IH), 4.75 (s, 2H), 3.64 (br s, IH)
36%
Stage #1: With n-butyllithium In hexane; toluene at -78℃; for 0.5 h;
Stage #2: at -78 - 0℃; for 0.333333 h; 		Manufacturing Example 41-1-1 (5-Fluoro-pyridin-2-yl)-methanol; To a solution of 2-bromo-5-fluoropyridine (3.67 g, 20.8 mmol) in toluene (100 mL) was added dropwise n-butyl lithium (15.6 mL, 1.6 M hexane solution, 25.0 mmol) under nitrogen atmosphere at -78° C., which was stirred for 30 minutes. N,N-Dimethylformamide (8.05 mL, 104.0 mmol) was added dropwise to this solution at -78° C., and stirred for 20 minutes at 0° C. This reaction solution was vigorously stirred after addition of water and tetrahydrofuran. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. Sodium borohydride (1.58 g, 41.8 mmol) was added to the filtrate at 0° C., and stirred for 1 hour at room temperature. This reaction solution was partitioned by addition of water and tetrahydrofuran. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:2) to obtain the title compound (945 mg, 36percent).1H-NMR Spectrum (CDCl3) δ (ppm): 4.75 (2H, s), 7.29 (1H, dd, J=4.4, 8.8 Hz), 7.43 (1H, ddd, J=2.8, 8.4, 8.4 Hz), 8.42 (1H, d, J=2.8 Hz).
References: [1] Patent: WO2007/2181, 2007, A2, . Location in patent: Page/Page column 162-163.
[2] Patent: US2009/82403, 2009, A1, . Location in patent: Page/Page column 89.
[3] Patent: US2007/72831, 2007, A1, . Location in patent: Page/Page column 97-98.
 

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