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Chemical Structure| 403-54-3 Chemical Structure| 403-54-3
Chemical Structure| 403-54-3

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Product Details of 3-Fluorobenzonitrile

CAS No. :403-54-3
Formula : C7H4FN
M.W : 121.11
SMILES Code : C1=C(C=CC=C1F)C#N
MDL No. :MFCD00001797
InChI Key :JZTPKAROPNTQQV-UHFFFAOYSA-N
Pubchem ID :67880

Safety of 3-Fluorobenzonitrile

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H301+H311+H331-H314-H412
Precautionary Statements:P280-P301+P310-P305+P351+P338
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of 3-Fluorobenzonitrile

* 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 [ 403-54-3 ]
  • Downstream synthetic route of [ 403-54-3 ]

[ 403-54-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 403-54-3 ]
  • [ 656235-44-8 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With Triisopropyl borate; lithium diisopropyl amide In tetrahydrofuran; hexane at -50 - -5℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; tert-butyl methyl ether at 20℃; for 0.5 h;
Intermediate 6; ψ-Cvano^-fluorophenylboronic acid; A 500 mL 3-neck, round bottom flask, equipped with a magnetic stirring bar, addition funnel, and nitrogen gas inlet, was charged with 3-fluorobenzonitrile (10.0 g, 82.56 mmol), triisopropyl borate (28.5 mL, 23.3 g, 123.84 mmol), and 100 mL of anhydrous THF. The mixture was cooled to -50 0C under nitrogen and a solution of LDA in THF/hexane (86.7 mmol, freshly prepared from 8.77 g of diisopropylamine in 20 mL of THF and 54.2 mL of a 1.6 M solution of n-BuLi in hexane) was added dropwise over a period of 1 h. The mixture was warmed to -5 0C and stirred for 30 min. Then 70 mL of 5 N HCIaq and 50 mL of MTBE was added and stirred for 30 min at room temperature. The mixture was extracted with MTBE (4x100 mL), the MTBE extract was washed with brine (2x100 mL), evaporated under reduced pressure keeping the temperature below 20 0C, and dried under vacuum at room temperature to give 12.16 g (89 percent) of δ-cyano^-fluorophenylboronic acid as a white solid. LCMS m/z (M+H)+: 165.8. 1H NMR (300 MHz, DMSO-d6): δ 8.92 (2H), 7.65 (1H), 7.57 (1H), 7.49 (1H).
References: [1] Patent: WO2006/51410, 2006, A1, . Location in patent: Page/Page column 44.
[2] Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 5938 - 5945.
[3] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 566 - 569.
 

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