Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 24955673 | HCID 24955673 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68556857 | HCID 68556857 | 99.4% |
Reaction Steps
A solution of {[4-(3-sec-butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester (0.8 g, 1.6 mmol) in CH2Cl2 (16 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 solution (4.8 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (25 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by column chromatography over flash silica gel (Hexane:Ethylacetate 90:10) to afford the pure product {[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester (0.77 g, 99% Yield)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420851B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-a07a54517784459697e369f6e23b0a93 |
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| Source note | uspto-grants-2013_04 |
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