Bromine → HCID 59143761, compound

HRID 417926Notes

Reaction equation

HRID 417926 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:8][NH:7][C:6](=[O:9])[CH2:5][C:4](=[O:10])[CH2:3]1.[Br:12]Br>C(O)(=O)C>[Br:12][CH:5]1[C:4](=[O:10])[CH2:3][C:2]([CH3:11])([CH3:1])[CH2:8][NH:7][C:6]1=[O:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 123492876,6-Dimethylazepane-2,4-dione

Product 1

HCID 59143761HCID 59143761, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6,6-dimethylazepan-2,4-dione (10.0 g, 64.5 mmol) in glacial acetic acid (160 mL) was added bromine (3.3 mL, 64.5 mmol) dropwise. The reaction mixture was stirred at r.t. for 1 h. The resulting precipitate was collected by filtration to give the title compound (16.83 g, quantitative) as a white solid. δH (DMSO-d6) 0.86 (3H, s), 0.99 (3H, s), 2.31 (1H, d, J 11.7 Hz), 2.73 (1H, d, J 11.7 Hz), 2.75 (1H, dd, J 15.2, 6.6 Hz), 3.31 (1H, dd, J 15.2, 6.6 Hz), 5.77 (1H, s), 8.40 (1H, t, J 6.2 Hz). LCMS (ES+) 234/236 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-93b56c39cb0b491dbad2883475121bdf
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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