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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1750825Generated: November 1, 2026

Ethyl Acetate → 1-Bromo-2-(2-(ethoxymethoxy)-1,3-difluoropropan-2-yl)-4-methylbenzene

https://huagongshe.com/reaction/1750825

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium hydrideHCID 24758—
Reactant1-(Chloromethoxy)-2-methoxyethaneHCID 77590—
Reactant2-(2-Bromo-5-methylphenyl)-1,3-difluoropropan-2-olHCID 86685073—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product1-Bromo-2-(2-(ethoxymethoxy)-1,3-difluoropropan-2-yl)-4-methylbenzeneHCID 8668507473.9%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09156860B2
Source datasetuspto-grants-2015_10
ORD IDord-ef8b92b0f98e4d2d87717b5e740d478f
Source noteuspto-grants-2015_10