Bromine → 2-Bromo-5-(4-chlorophenyl)cyclohexane-1,3-dione

HRID 1364085Notes

Reaction equation

HRID 1364085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Br:16]Br>CC(O)=O>[Br:16][CH:11]1[C:12](=[O:14])[CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9][C:10]1=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 7295015-(4-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 669326572-Bromo-5-(4-chlorophenyl)cyclohexane-1,3-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 5-(4-chlorophenyl)cyclohexane-1,3-dione (5 g, 22.6 mmol) in AcOH (40 mL) at r.t. was added bromine (3.61 g, 1.15 mL, 22.6 mmol) dropwise. The reaction was then carried out according to Method A to give the title compound (2.0 g, 66%) as a white solid. δH (DMSO-d6) 7.38 (4H, m), 3.41-3.38 (1H, m), 2.97-2.85 (2H, m), 2.67 (2H, dd, J 16.4 and 4.2 Hz), 2.50 (1H, bs).

Sources & evidence

ORD record
ord-4d4f5d258dcf4cf8b9523a4d1293db05
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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