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Chemical Structure| 503315-74-0
Chemical Structure| 503315-74-0
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Product Details of [ 503315-74-0 ]

CAS No. :503315-74-0 MDL No. :MFCD03094236
Formula : C7H6FNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FEMLPDPJKINFGA-UHFFFAOYSA-N
M.W : 171.13 Pubchem ID :2774658
Synonyms :

Safety of [ 503315-74-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 503315-74-0 ]

* 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 [ 503315-74-0 ]
  • Downstream synthetic route of [ 503315-74-0 ]

[ 503315-74-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 503315-74-0 ]
  • [ 403-21-4 ]
YieldReaction ConditionsOperation in experiment
92% With jones reagent; calcium carbonate In water; acetone at 0℃; for 0.5 h; In the step D-3, to a solution of 3-fluoro-4-nitrobenzyl alcohol (2. 97 g) in acetone (60 ml) was added Jones reagent (13 ml), prepared from CHROMIC acid (26.7 g) and sulfuric acid (23 ml) in water (100 ml), dropwise at 0C. The mixture was stirred on a ice-bath for 0.5 hours and quenched with isopropanol (20 ml) to be concentrated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and washed with water (30 ml X 3), and brine (30 ml X 1), successively. The organic layer was dried over sodium sulfate and concen- trated in vacuo to obtain a yellow solid, that was triturated with hexane to give 3-FLUORO-4-NITROBENZOIC acid as a pale yellow solid (2.94 g, 92percent).
Reference: [1] Patent: WO2004/58764, 2004, A1, . Location in patent: Page 39
  • 2
  • [ 503315-74-0 ]
  • [ 160538-51-2 ]
YieldReaction ConditionsOperation in experiment
66% With manganese(IV) oxide In dichloromethane at 20℃; [3-FLUORO 4-NITRO BENZYL ALCOHOL (116MG, 0. 68MMOL, LEQ. ) WAS DISSOLVED IN DCM (10ML)] and treated with Mn02 (580mg, 6. [73MMOL,] [LOEQ.)] and the suspension stirred at room temperature over night. [MN02] was filtered off the suspension using celite and the solvent evaporated to give the corresponding aldehyde as a white solid (66percent yield). [IH] NMR: 8= (400 MHz, [CDCL3)] : 9.98 (s, [1H,] [CHO),] 8.08 [(M,] [1H,] ArH), 7.78 [(M,] 2H, ArH).
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 65-66
  • 3
  • [ 403-21-4 ]
  • [ 503315-74-0 ]
YieldReaction ConditionsOperation in experiment
97% With dimethylsulfide borane complex In tetrahydrofuran at 0 - 65℃; for 21 h; Part A. Preparation of (3-fluoro-4-nitrophenyl)methanol.; [00722]To a solution of 3-fluoro-4-nitrobenzoic acid (2.0 g, 10.8mmol) in TηF (50ml) at O0C was addedBH3-Me2S complex (2.215ml, 22.15mmol) drop-wise. The mixture was stirred at O0C for 3h, and was then stirred at 650C for 18h. To the cooled mixture was added ice (5Og), followed by 1 ν aq. HCl(100ml), and the resulting mixture was extracted with EtOAc (200ml). The organic layer was dried overνa24, filtered and concentrated in vacuo to provide the title compound as a white solid (1.79g, 97percent).
94%
Stage #1: With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 1 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
General method for the synthesis of 4-nitro-benzyl alcohols (III)To a solution of substituted 4-nitrobenzoic acid II (1.0 mmol) in THF (10 mL) was added HOBt (135 mg, 1.0 mmol) and DCC (227 mg, 1.1 mmol). The resulting mixture was stirred at room temperature for 1 h. The white precipitates were filtered off and rinsed with THF (2 x 5 mL). The filtrate was added dropwise to a suspension of NaBH4 (38 mg, 1.0 mmol) in THF (10 mL) over 30 min. The reaction was carried out at room temperature for additional 1.5 h and quenched by adding 10 mL 1.0 N HC1. After evaporation of THF under reduced pressure, the remaining aqueous solution was extracted EtOAc (3 x 20 mL). The combined EtOAc phase was washed with water and brine, and dried over Na2S04. After removal of Na2S04 via filtration, the filtrate was concentrated to dryness. The crude product was purified by flash column chromatography (hexane to 50percent EtOAc/hexane) to afford the desired alcohol III.3-Fluoro-4-nitrobenzyl alcohol. A yellow solid (161 mg, 94percent); 1H NMR (200 MHz, CDC13): δ 8.01 (t, 1H, J= 7.8 Hz), 7.29 (d, 1H, J= 1 1.8 Hz), 7.22 (d, 1H, J= 8.4 Hz), 4.77 (s, 2H), 2.00 (s, -OH); 13C NMR (50 MHz, CDC13): 155.7 (d, J= 265.0 Hz), 150.3 (t, J= 8.0 Hz), 136.9 (t, J= 8.0 Hz), 126.2 (d, J= 2.0 Hz), 121.7 (d, J= 4.0 Hz), 115.8 (d, J= 21.0 Hz), 63.4; lR (KBr): 2146, 1691 , 1432, 1298 cm"1.
92% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; TO AN ICE-COOLED SUSPENSION OF NABH4 (204MG, 5.4MMOL, 2EQ. ) IN THF (LOML) WAS ADDED
DROPWISE 3-FLUORO 4-NITRO BENZOIC ACID (500MG, 2. 7MMOL, LEQ. ) IN THF (IOML) OVER 30] minutes. BF3-Et20 (7.3mmol, 2.7eq.) was then added dropwise over 30 minutes. The solution was stirred at room temperature over night. IN [HC1] was added dropwise to quench NaBH4 excess. The solvent was [REMOVED IN VACTIO,] the residue dissolved in DCM, washed with water, brine. The organic layer was then dried over [MGS04] and the solvent removed in vacuo to give 425 mg of 3-fluoro 4-nitro benzyl alcohol (92percent yield). The compound was used in the following step with no further purification. [1H NMR] : [8=] (400 MHz, [CDC13)] : 7.97 [(M,] 1H), 7.28 [(M,] 1H), 7.18 [(M,] 1H), 4.75 [(M,] 2H).
Reference: [1] Patent: WO2009/39135, 2009, A1, . Location in patent: Page/Page column 140
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1153 - 1163
[3] Patent: WO2011/66416, 2011, A1, . Location in patent: Page/Page column 16
[4] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 65
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3986 - 3991
  • 4
  • [ 131858-37-2 ]
  • [ 503315-74-0 ]
YieldReaction ConditionsOperation in experiment
83% With calcium carbonate In 1,4-dioxane; waterHeating / reflux In the step D-2, a mixture of 3-fluoro-4-nitrobenzyl bromide (3.43 g) and calcium carbonate (7.63 g) in a mixture of water (40 ml) and 1,4-dioxane (40 ml) was refluxed overnight. After cooling to room temperature, the reaction mixture was passed through a paper filter to remove insoluble materials, that were washed with 1,4-dioxane (20ML). The filtrates were combined and evaporated in vacuo. The residue was dissolved in ethyl acetate (40 ml) and washed with IN hydrochloric acid, saturated sodium bicarbonate water solution and brine, successively, to be dried over sodium sulfate. When the solvent was removed in vacuo and the residue was triturated with hexane, 3-fluoro-4-nitrobenzyl alcohol was obtained as colorless powders (2.07 g, 83percent).
Reference: [1] Patent: WO2004/58764, 2004, A1, . Location in patent: Page 38
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