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CAS No. : | 438050-27-2 | MDL No. : | MFCD06202824 |
Formula : | C7H6FIO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 252.02 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
99% | Stage #1: 2-Fluoro-5-iodo-benzaldehyde With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.33333h; Stage #2: With water In ethyl acetate | 17.1 Step 1) (2-Fluoro-5-iodo-phenyl)-methanol Step 1) (2-Fluoro-5-iodo-phenyl)-methanol To an ice cooled solution of 2-Fluoro-5-iodo-benzaldehyde (1.0 g, 4.0 mmol) in CH3OH (10 mL) was added NaBH4 (0.182 g, 4.8 mmol) in two portions over 10 min. The reaction mixture was stirred for 1 h and concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed sequentially with 2*H2O (20 mL) and brine (20 mL). The organic layer was dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (30% Ethyl acetate/Petroleum Ether) to afford the titled compound (1.0 g, 99%) as a white solid, identified by NMR and mass spectral analyses. Mp: 42° C. MS (EI+): 252 (M+). |
88% | With sodium tetrahydroborate In tetrahydrofuran; methanol | 33 Dissolve 2-fluoro-5-iodobenzaldehyde, (prepared essentially as described in Tet. Lett., 33, 7499, (1992)), (6. 54 g, 26. 1 mmol) in 4 : 1 tetrahydrofuran : methanol (200 mL) and treat with sodium borohydride (1. 98 g, 52. 3 mmol) and stir overnight. Concentrate the reaction mixture, then partition between ethyl acetate and water. Wash the organic layer with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter, and concentrate. Purify the crude oil by silica gel chromatography, eluting with 85 : 15 hexanes : ethyl acetate, to give the title compound as a white crystalline solid (5. 8 g, 88%). 1HNMR (400 MHz, DMSO-d6) 6 4. 46 (d, J = 5. 7 Hz, 2H), 5. 31 (t, J = 5. 7 Hz, 1H), 6. 96 (dd, J = 10. 1, 8. 8 Hz, 1H), 7. 58 (ddd, J = 8. 6, 4. 8, 2. 4 Hz, 1H), 7. 72 (dd, J = 6. 8, 2. 4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With borane-THF; In tetrahydrofuran; at 0 - 70℃; for 2h;Inert atmosphere; | General procedure: General method G for the synthesis of 3-benzyl morpholines of Structure 1(2-Fluoro-5-iodo-phenyl)-methanol (G-6)Borane.THF complex 1 M soln. (94 mL, 94 mmol) was added dropwise to a 0C suspension of <strong>[124700-41-0]2-fluoro-5-iodobenzoic acid</strong> (10 g, 37.6 mmol) in THF (60 mL) under argon and after complete addition the reaction mixture was heated to 70C for 2h. The reaction mixture was cooled to 0C and quenched with MeOH and after stirring for 5 min the reaction mixture was evaporated in vacuo. The residue was partitioned between 2M aq. HCI and MeOH and stirred for 30 min at 50C before being concentrated in vacuo. The remaining aqueous phase was diluted with additional water and extracted with DCM (3x). The combined organic extracts were dried (Na2S04), filtered and evaporated in vacuo to give the title compound as a yellow solid that was used further without purification. LC-MS B: tR = 0.66 min; [M+H+Na]+ = 275.99; 1 H NMR (DMSO) deltaEta: 7.77 (dd, ^ = 7.0 Hz, J2 = 2.3 Hz, 1 H), 7.64 (m, 1 H), 7.01 (dd, = 10.1 Hz, J2 = 8.6 Hz, 1 H), 5.38 (t, J = 5.8 Hz, 1 H), 4.52 (d, J = 5.8 Hz, 2 H). | |
With borane-THF; In tetrahydrofuran; at 0 - 70℃; for 2h;Inert atmosphere; | (2-Fluoro-5-iodo-phenyl)-methanol (G-6) Borane.THF complex 1M soln. (94 mL, 94 mmol) was added dropwise to a 0 C. suspension of <strong>[124700-41-0]2-fluoro-5-iodobenzoic acid</strong> (10 g, 37.6 mmol) in THF (60 mL) under argon and after complete addition the reaction mixture was heated to 70 C. for 2 h. The reaction mixture was cooled to 0 C. and quenched with MeOH and after stirring for 5 min the reaction mixture was evaporated in vacuo. The residue was partitioned between 2M aq. HCl and MeOH and stirred for 30 min at 50 C. before being concentrated in vacuo. The remaining aqueous phase was diluted with additional water and extracted with DCM (3*). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow solid that was used further without purification. LC-MS B: tR=0.66 min; [M+H+Na]+=275.99; 1H NMR (DMSO) deltaH: 7.77 (dd, J1=7.0 Hz, J2=2.3 Hz, 1H), 7.64 (m, 1H), 7.01 (dd, J1=10.1 Hz, J2=8.6 Hz, 1H), 5.38 (t, J=5.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H). |