1,2-Dibromoethane → HCID 59272426, compound

HRID 1875364Notes

Reaction equation

HRID 1875364 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])=[O:3].C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26]Br>>[C:2]([C:4]1[C:9]([O:10][CH2:26][CH2:25][Br:24])=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])(=[O:3])[CH3:1]

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 68086Khellinone

Product 1

HCID 59272426HCID 59272426, compoundYield 83%

Procedure

Khellinone (850 mg, 3.6 mmol, 0.4 M), K2CO3 (3 eqs) and 1,2-dibromoethane (3 eqs) were reacted according to General Procedure A. The crude product was purified by flash chromatography, eluting with ethyl acetate:petroleum ether (15:85) to afford the title compound as a clear oil (1.02 g, 83%). 1H NMR (300 MHz, CDCl3): δ 2.53 (s, 3H), 3.57 (t, J=6.3 Hz, 2H), 3.98 (s, 3H), 4.07 (s, 3H), 4.35 (t, J=6.3 Hz, 2H), 6.86 (d, J=2.2 Hz, 1H), 7.57 (d, J=2.2 Hz, 1H). MS (ES+) m/z 342.8/344.8 (M+H+).

Workup

  1. customThe crude product was purified by flash chromatography
  2. washeluting with ethyl acetate:petroleum ether (15:85)

Sources & evidence

ORD record
ord-fc5711b464a647a08b8aa311f7b15acf
Source dataset
uspto-grants-2012_11
Patent number
US08309545B2

Reaction notes

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