N-bromobutanimide → 2-Bromo-1-morpholin-4-yl-butane-1,3-dione

HRID 579444Notes

Reaction equation

HRID 579444 reaction equation
[N:1]1([C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:13]N1C(=O)CCC1=O>ClCCCl>[Br:13][CH:8]([C:9](=[O:11])[CH3:10])[C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 855504-(1,3-Dioxobutyl)morpholine

Product 1

HCID 866834242-Bromo-1-morpholin-4-yl-butane-1,3-dioneYield 98.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-morpholin-4-yl-butane-1,3-dione (0.53 g, 3.1 mmol) in 1,2-dichloroethane (30 mL) stirred at 0° C., N-bromosuccinimide (0.55 mg, 3.1 mmol) was added in small portions and the mixture was stirred for 1 h. The solution was washed with brine (3×5 mL), dried over MgSO4 and concentrated below 30° C. 2-Bromo-1-morpholin-4-yl-butane-1,3-dione 0.76 g, 3.04 mmol, 98.1%, LCMS/BB_LCMS01(+)/: M+1=250, 252, Rt: 1.831 min] was obtained as a yellowish oil.

Workup

  1. washThe solution was washed with brine (3×5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated below 30° C

Sources & evidence

ORD record
ord-c3e4f7c87be047c9b1b06ebcd0d0c235
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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