Bromine → HCID 58194817, compound

HRID 1753943Notes

Reaction equation

HRID 1753943 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) 811.2, 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-b1bcf28e3f8241859fc49edf65525dd8
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

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