Bromine → HCID 58194817, compound

HRID 628723Notes

Reaction equation

HRID 628723 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[O:6]=[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]([OH:15])=O.[Br:16]Br>C(OCC)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:13]([CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([Br:16])[C:7]1=[O:6])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 66679012HCID 66679012, compound

Product 1

HCID 58194817HCID 58194817, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2-oxo-cyclohexanecarboxylic acid diethylamine (3.56 mL, 19.3 mmol) was dissolved in diethyl ether (5 mL) and cooled with stirred to 0° C. under N2. Bromine (0.99 mL, 19.3 mmol) was added drop wise over 15 minutes and the reaction mixture was allowed to warm to room temperature over 3 hours. A solid had precipitated out of the reaction. It was collected by filtration and washed with ether to give 5.85 g (109%) of 3-Bromo-2-oxo-cyclohexanecarboxylic acid diethylamide (35) as a pale yellow solid. The structure was confirmed by 13C NMR (CDCl3) δ11.2, 12.8, 22.7, 28.8, 37.6, 37.9, 39.4, 51.0, 55.7, 165.5, 197.2

Workup

  1. temperaturecooled
  2. temperatureto warm to room temperature over 3 hours
  3. customA solid had precipitated out of the reaction
  4. filtrationIt was collected by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-c7f42612d76b4643806d5948691a376c
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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