Abstract: Abstract: The present invention relates to an advantageous, industrially feasible process for preparing (S)-3-(4-(2-chloro-5-iodobenzyl)phenoxy) tetrahydrofuran.
Claims:
(1) A novel process for preparing (S)-3-(4-(2-chloro-5-iodobenzyl)phenoxy) tetrahydrofuran of formula-2 comprising the steps of;
Formula-2
(a) reacting 2-Chloro-5-iodobenzoic acid with oxalyl chloride in presence of solvent, catalyst
(b) alkylating with fluorobenzene in presence of lewis acid
(c) isolating 2-Chloro-4'-fluoro-5-iodobenzophenone
(d) reducing 2-Chloro-4'-fluoro-5-iodobenzophenone in presence of solvent and reducing agent
(e) isolating l-Chloro-2-(4-fluorobenzyl)-4-iodobenzene
(f) reacting l-Chloro-2-(4-fluorobenzyl)-4-iodobenzene with (S)-3-hydroxytetrahydrofuran in presence of base and solvent
(g) isolating (S)-3-(4-(2-chloro-5-iodobenzyl)phenoxy)tetrahydrofuran
(2) The process according to claim 1, wherein the solvent is selected from the group consisting of dichloromethane, ethyl acetate, tetrahydrofuran, acetone, acetonitrile, Dimethylformamide, dimethylsulfoxide and mixture thereof.
(3) The process according to claim 1, wherein the catalyst is Dimethylformamide.
(4) The process according to claim 1, wherein the lewis acid is selected from the group consisting of boron trifluoride ether, trisperfluorophenyl boron Alkane, trifluoroacetic acid, hydrogen chloride and its solutions, hydrogen bromide and its solutions, aluminum trichloride, indium trichloride.
(5) The process according to claim 1, wherein the reducing agent is selected from the group consisting of silane such as triethylsilane, trimethylsilane, tri-n-propylsilane, or tri isopropy 1 si lane, 1,1,3,3-tetramethyldisiloxane, borohydride such as sodium borohydride , Potassium borohydride, or borane; or aluminum hydride such as lithium aluminum hydride. (6) The process according to claim 1, wherein the base is selected from the group consisting of alcohol bases or phenol bases, carbonate bases, alkali metal hydroxides, C1-C3 tertiary amines, or other nitrogen-containing organic bases. The base is selected from the group consisting of Potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium carbonate, sodium carbonate, cesium carbonate, potassium hydroxide, sodium hydroxide, triethylamine, two Isopropylethylamine, sodium hexamethyldisilylamide, lithium hexamethyldisilylamide, potassium hexamethyldisilylamide, l,8-diazabicyclo[5.4.0] eleven Carbon-7-ene (DBU), triethylene diamine (DABCO) or mixture thereof.
| # | Name | Date |
|---|---|---|
| 1 | 202041042010-Form5_(As Filed)_28-09-2020.pdf | 2020-09-28 |
| 2 | 202041042010-Form3_(As Filed)_28-09-2020.pdf | 2020-09-28 |
| 3 | 202041042010-Form26_Power of Attorney_28-09-2020.pdf | 2020-09-28 |
| 4 | 202041042010-Form2 (Title Page)_Provisional_28-09-2020.pdf | 2020-09-28 |
| 5 | 202041042010-Form1_(As Filed)_28-09-2020.pdf | 2020-09-28 |
| 6 | 202041042010-Description Provisional_(As Filed)_28-09-2020.pdf | 2020-09-28 |
| 7 | 202041042010-Correspondence_28-09-2020.pdf | 2020-09-28 |
| 8 | 202041042010-Form5_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 9 | 202041042010-Form3_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 10 | 202041042010-Form2 Title Page_Complete_10-08-2021.pdf | 2021-08-10 |
| 11 | 202041042010-Form1_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 12 | 202041042010-Description Complete__Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 13 | 202041042010-Correspondence_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 14 | 202041042010-Claims_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |
| 15 | 202041042010-Abstract_Complete After Provisional_10-08-2021.pdf | 2021-08-10 |