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CAS No. : | 14473-91-7 | MDL No. : | MFCD00004382 |
Formula : | C9H7BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YEMUSDCFQUBPAL-SNAWJCMRSA-N |
M.W : | 227.05 | Pubchem ID : | 776461 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3 h; Stage #2: With sodium hydroxide; water In diethyl ether |
To suspension Of LiAlH4 (0.5 g, 1.3 mmol) in diethyl ether (25 mL) was added 3- bromocinnamic acid (83, 1.0 g, 4 mmol), in portions, at RT. The resulting suspension was stirred for 3 hours. The reaction was quenched by the successive addition of 15percent aq. NaOH solution (1 mL) and water. The resulting white suspension was filtered through a pad of Celite. The filter cake was washed with ether and then ethyl acetate. The filtrate was concentrated to afford crude 8 as yellow oil. Yield (0.7g, 74percent). 1H NMR (400 MHz, CDCl3) δ 7.10-7.35 (m, 4H), 3.65 (t, J = 6.5 Hz, 2H), 2.68 (t, J = 7.8 Hz, 2H), 1.82-1.91 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With trans-N,N'-dimethylcyclohexane-1,2-diamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide In 1,4-dioxane at 110℃; for 22 h; | A Schlenk tube was charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), 3- bromocinnamic acid (228 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Racemic trans-N,N'-dimethyl-1, 2-cyclohexanediamine (16 μL, 0.10 mmol, 10 molpercent), 1,1, 1,3, 3, [3-HEXAMETHYLDISILAZANE] (211 [I1L,] 1.00 mmol), and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 22 h. The resulting suspension was allowed to reach room temperature, poured into ether (20 mL), and washed with a solution of Na2S205 (100 mg) in 10percent aq [HC1] [(3X20] mL). The organic phase was dried [(NA2SO4)] and concentrated. The residue was dissolved in hot ethanol (5 mL), and hot water (5 mL) was added to the solution. The product was allowed to crystallize at 0 [C] for 15 h to provide 256 mg (93percent yield) of 3-iodocinnamic as pale yellow needles. Mp: [186-188 °C] (lit. 180- [182 °C] See Yuzikhin, [O.] S.; Vasil'ev, A. V.; Rudenko, A. P. [RUSS. J ORG. CLIENI.] 2000, 36, [1743). 1H] NMR (400 MHz, DMSO-d6): 8 12.47 (s, 1H), 8.08 (s, 1H), 7.77 (d, J= 7.8 Hz, 1 H), 7.72 (d, [J=] 7.8 Hz, [1H),] 7.52 (d, [J=] 16.0 Hz, 1 H), 7.22 (t, [J= 7.] 8 Hz, [1H),] 6.5 8 (d, J = 16.0 Hz, 1H). [13C] NMR (100 MHz, DMSO-d6) : 8 167.3, 142.3, 138.6, 136.6, 136.5, 130.9, 127.4, 120.6, 95.4. |
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