HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 1-Bromo-2-(2-(ethoxymethoxy)-1,3-difluoropropan-2-yl)-4-methylbenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-(Chloromethoxy)-2-methoxyethane | HCID 77590 | — |
| Reactant | 2-(2-Bromo-5-methylphenyl)-1,3-difluoropropan-2-ol | HCID 86685073 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-Bromo-2-(2-(ethoxymethoxy)-1,3-difluoropropan-2-yl)-4-methylbenzene | HCID 86685074 | 73.9% |
Reaction Steps
NaH (362 mg, 9.05 mmol) was added to a solution of 2-(2-bromo-5-methylphenyl)-1,3-difluoropropan-2-ol (2.0 g, 7.54 mmol) in THF (10 mL) slowly at 0° C. MEMCl (1.41 g, 11.32 mmol) was added dropwise. The mixture was stirred at rt overnight. The mixture was diluted with H2O and extracted with EA (50 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (10:1 to 6:1) to give the product (1.8 g, yield 68%) as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09156860B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-ef8b92b0f98e4d2d87717b5e740d478f |
| Source note | uspto-grants-2015_10 |