N-bromobutanimide → 2-Bromo-5-(2-furyl)cyclohexane-1,3-dione

HRID 1364090Notes

Reaction equation

HRID 1364090 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]1.[Br:14]N1C(=O)CCC1=O>C1COCC1>[Br:14][CH:9]1[C:10](=[O:12])[CH2:11][CH:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH2:7][C:8]1=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6995135-(2-Furyl)cyclohexane-1,3-dione

Product 1

HCID 669330292-Bromo-5-(2-furyl)cyclohexane-1,3-dioneYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 5-(2-furyl)cyclohexane-1,3-dione (1 g, 5.6 mmol) in THF (50 mL) was added N-bromosuccinimide (1 g, 5.6 mmol). The reaction mixture was heated to 85° C. for 12 h and on completion was filtered. The filtrate was concentrated in vacuo to give the title compound (1.0 g, 69%) as a white solid. LCMS (ES+) 256.8 (M+H)+.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-96a95017985646df8c7cf129f17477eb
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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