Bromine → HCID 90142044, compound

HRID 1025928Notes

Reaction equation

HRID 1025928 reaction equation
[Cl:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[Br:10]Br>[OH-].[Na+]>[Br:10][N:4]1[C:3]([CH2:2][Cl:1])([CH3:9])[CH2:7][O:6][C:5]1=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 90142044HCID 90142044, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (2.70 g, 18.1 mmol) in 1.0 M NaOH (20 ml) was cooled to 0° C. Bromine (1.0 ml, 20 mmol) was added dropwise, and stirred for 30 min. The precipitate was filtered off to give the title compound (2.32 g, 10.2 mmol, 56%). 1H NMR (CDCl3, 400 MHz) δ 1.44 (s, 3H), 3.49 (d, J=12.0 Hz, 1H), 3.65 (d, J=12.0 Hz, 1H), 4.22 (d, J=8.8 Hz, 1H), 4.57 (d, J=8.4 Hz, 1H). LRMS (ESI/APCI): 228 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-964bc41f396f4e8796c54b8e87a0848d
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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