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CAS RN: 4525-65-9 | Numéro de produit: T3121
2,4,6-Trichlorophenyl Formate
Pureté: >97.0%(HPLC)
- Formic Acid 2,4,6-Trichlorophenyl Ester
Taille | Prix unitaire | Philadelphia, PA | Portland, OR | Japon * | Quantité |
---|---|---|---|---|---|
1G |
$33.00
|
1 | 3 | 9 |
|
5G |
$82.00
|
13 | 2 | ≥80 |
|
*Les articles en stock localement sont expédiés dans un délai de 1 à 2 jours. Les articles en stock au Japon peuvent être expédiés depuis un entrepôt aux Etats-Unis dans un délai de 2 semaines. Veuillez contacter TCI pour connaître les délais de livraison des articles qui ne sont pas en stock. Cela ne concerne par les articles réglementés et les articles expédiés sur carboglace.
Numéro de produit | T3121 |
Pureté / Méthode d'analyse | >97.0%(HPLC) |
Formule moléculaire / poids moléculaire | C__7H__3Cl__3O__2 = 225.45 |
Etat physique (20 ° C) | Solid |
Condition de stockage | Room Temperature (Recommended in a cool and dark place, <15°C) |
CAS RN | 4525-65-9 |
Numéro de registre de Reaxys | 2524466 |
Identifiant de la substance PubChem | 253661984 |
Appearance | White to Almost white powder to crystal |
Purity(HPLC) | min. 97.0 area% |
Purity(Argentometric Titration) | min. 95.0 % |
Melting point | 81.0 to 85.0 °C |
Point de fusion | 83 °C |
Solubilité (soluble dans) | Toluene |
Numéro du SH (importation) (TCI-A) | 2915.13.1000 |
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Used Chemicals
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Procedure
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A solution of 2-iodofluorene (500 mg, 1.71 mmol), 2,4,6-trichlorophenyl formate (579 mg, 2.57 mmol), palladium(II) acetate (38.4 mg, 0.171 mmol), Xantphos (198 mg, 0.342 mmol) and triethylamine (470 µL, 3.42 mmol) in toluene (10 mL) was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue was washed with acetonitrile to give 1 as a pale yellow solid (462 mg, 69% yield).
A solution of 1 (460 mg, 1.18 mmol), triethylamine (330 µL, 2.36 mmol), DMAP (7.2 mg, 59 µmol) and morpholine (154 µL, 1.77 mmol) in THF (5 mL) was stirred at 45 °C for 20 hours. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 0:100 - 50:50) to give 2 as a white solid (305 mg, 93% yield).
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Experimenter’s Comments
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The reaction mixture at the first step was monitored by TLC (hexane:ethyl acetate = 1:19, Rf = 0.34).
The reaction mixture at the second step was monitored by TLC (hexane:ethyl acetate = 1:1, Rf = 0.26).
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Analytical Data
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2,4,6-Trichlorophenyl 9H-Fluorene-2-carboxylate (1)
(9H-Fluoren-2-yl)(morpholino)methanone (2)1H NMR (400 MHz, CDCl3);
(1) δ 8.41 (s, 1H), 8.29 (d, J = 8.1 Hz, 1H), 7.94-7.88 (m, 2H), 7.62 (d, J = 6.2 Hz, 1H), 7.48–7.38 (m, 4H), 4.02 (s, 2H).
(2) δ 7.81 (d, J = 7.6 Hz, 2H), 7.62-7.56 (m, 2H), 7.43-7.32 (m, 3H), 3.94 (s, 2H), 3.72 (brs, 8H). -
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Lead Reference
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- Trichlorophenyl Formate: Highly Reactive and Easily Accessible Crystalline CO Surrogate for Palladium-Catalyzed Carbonylation of Aryl/Alkenyl Halides and Triflates.
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Other References
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- Pd-Catalyzed External-CO-Free Carbonylation: Preparation of 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate
- Formic Acid Derivatives as Practical Carbon Monoxide Surrogates for Metal-Catalyzed Carbonylation Reactions
References
- 1)T. Ueda, H. Konishi, K. Manabe, Org. Lett. 2012, 14, 5370.
- 2)H. Konishi, T. Ueda, K. Manabe, Org. Synth. 2014, 91, 39.
- 3)H. Konishi, K. Manabe, Synlett 2014, 25, 1971.
Articles / Brochures
[TCI Practical Example] Introduction of Carbonyl Group by Using 2,4,6-Trichlorophenyl Formate
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