1-(4-Bromo-3-nitrophenyl)ethan-1-one → 1-[4-(4,4-Dimethyl-cyclohex-1-enyl)-3-nitro-phenyl]-ethanone

HRID 1711254Notes

Reaction equation

HRID 1711254 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][C:15]1([CH3:24])[CH2:20][CH2:19][C:18](B(O)O)=[CH:17][CH2:16]1>CCOC(C)=O.CCCCCC>[CH3:14][C:15]1([CH3:24])[CH2:20][CH2:19][C:18]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])=[CH:17][CH2:16]1

Participants

4

Reactant 2

HCID 877371-(4-Bromo-3-nitrophenyl)ethan-1-oneHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acid

Product 1

HCID 587548131-[4-(4,4-Dimethyl-cyclohex-1-enyl)-3-nitro-phenyl]-ethanoneYield 99.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 11, step (e) using 1-(4-bromo-3-nitro-phenyl)-ethanone (347 mg, 1.42 mmol), and 4,4-dimethylcyclohexen-1-ylboronic acid (254 mg, 1.65 mmol). Silica gel chromatography (5-15% EtOAc/hexane) afforded the title compound (385 mg, 99%) as a faint green oil. Mass spectrum (APCI, m/z): Calcd. for C16H19NO3, 274.1 (M+H), found 274.0.

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 11, step (e)

Sources & evidence

ORD record
ord-61e10964513f49659af0071a7f74411b
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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