Bromine → 3-Bromo-2-hydroxy-5-methyl-cyclohex-1-enecarboxylic acid diethylamide

HRID 1629622Notes

Reaction equation

[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])[CH3:2].[Br:16]Br>C(OCC)C>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH:8]([Br:16])[C:7]=1[OH:13])=[O:5])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

5-methyl-2-oxo-cyclohexanecarboxylic acid diethylamide (46) (4.4 g, 21 mmol) was dissolved in diethyl ether (5 mL) and cooled to 0° C. under N2. Bromine (3.32 g, 21 mmol, 1.1 mL) was added dropwise over 15 min and the reaction mixture was allowed to warm to room temperature over 90 min. The mixture was slowly poured into ice-cold saturated aqueous sodium carbonate solution (40 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layers were dried and concentrated in vacuo to afford 6.1 g (quantitative) of 3-bromo-2-hydroxy-5-methyl-cyclohex-1-enecarboxylic acid diethylamide (47) as an off-white solid. The structure was confirmed by 1H NMR (300 MHz, CDCl3) δH 0.8-1.20 (9H, m, CH3 and N(CH2CH3)2), 1.80-2.40 (5H, m, CH2CH(CH3)CH2), 3.15-3.55 (4H, m, N(CH2CH3)2), 4.65-4.74 (1H, m, CHBr), and 12.04 (1H, s, OH).

Workup

temperatureto warm to room temperature over 90 min
extractionextracted with ethyl acetate (3×40 mL)
customThe combined organic layers were dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ba64bfae5d9d4e3d811170a624a35c4e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08790619B2

Reaction notes

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