Water → 1-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone

HRID 38999

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([O:11][CH2:13][CH:15]2[CH2:16][O:17]2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95).

Workup

customwas brought to ambient temperature
extractionThe water phase was extracted with EtOAc
washThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
dry with materialwere dried (Na2SO4)
customevaporated to dryness
customPurification on flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record: ord-2c0dfc5a21934582bc955561daae8b21
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Linked notes

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