1,2-Cyclohexanedione → 3-Bromocyclohexane-1,2-dione

HRID 1803212Notes

Reaction equation

HRID 1803212 reaction equation
[Br:1]Br.[C:3]1(=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:8]1[CH2:7][CH2:6][CH2:5][C:4](=[O:9])[C:3]1=[O:10]

Participants

4

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 24408Bromine

Product 1

HCID 134385013-Bromocyclohexane-1,2-dione

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Step AAE (1): Followed the method of B. Miller and H.-S. Wong Tetrahedron 1972, 28, 2369. Bromine (0.651 mL, 12.6 mmol) in was added dropwise to a solution of cyclohexane-1,2-dione (1.35 g, 12.0 mmol) in CCl4 (30 mL) at 0° C. The reaction mixture was allowed to warm to rt. The resulting solution was concentrated in vacuo to afford 3-bromocyclohexane-1,2-dione. The crude product, which is prone to decomposition, was used for subsequent chemistry without purification or characterization.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-914c2c6143dd4dd2afa24eeb54052343
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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