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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1399832Generated: November 2, 2026

Water → 2-[(3-Bromophenoxy)methyl]oxirane

https://huagongshe.com/reaction/1399832

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant3-BromophenolHCID 11563—
ReactantEpibromohydrinHCID 18430—
ReactantSodium hydrideHCID 24758—
SolventDimethylformamideHCID 6228—
Product2-[(3-Bromophenoxy)methyl]oxiraneHCID 3865342113.3%

Reaction Conditions

Temperature20 °C

Reaction Steps

To a solution of compound NaH (416.2 mg, 17.34 mmol) in DMF (10 mL) was added 3-bromophenol (1.0 g, 5.78 mmol) at 20° C. After addition the solution was stirred for 5 minutes at this temperature before the addition of 2-(bromomethyl)oxirane (1.2 g, 8.67 mmol). The reaction mixture was stirred for 16 h at 20° C. Once complete the reaction mixture was treated with water (50 mL) and extracted with EA (2×20 mL) and the organic layers combined and washed with NaHCO3, brine (30 mL), dried over Na2SO4 and concentrated to give the compound 2-((3-bromophenoxy)methyl)oxirane (1.5 g, crude) as colorless oil which was used in next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08906900B2
Source datasetuspto-grants-2014_12
ORD IDord-c36ef686203b46e098d17c307c600010
Source noteuspto-grants-2014_12