1-Phenyl-1,2-propanedione → 3-Bromo-1-phenylpropane-1,2-dione

HRID 1162552Notes

Reaction equation

HRID 1162552 reaction equation
[C:1]1([C:7](=[O:11])[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]Br>ClCCCl>[Br:12][CH2:9][C:8](=[O:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:11]

Participants

4

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 24408Bromine

Product 1

HCID 125689113-Bromo-1-phenylpropane-1,2-dioneYield 121.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-phenyl-propane-1,2-dione (1.72 g, 0.0116 mol) in DCE (5 mL) was added Br2 (1.87 g, 0.0169 mol). The reaction mixture was stirred for 75 min. and the volatiles were removed to yield 3.21 g of 3-bromo-1-phenyl-propane-1,2-dione. The crude bromoketone (0.1046 mol) was combined at room temperature with 3-(1-cyclopentyl-thioureido)-propionic acid tert-butyl ester (7.00 g, 0.031 mol) in NMP (50 mL) following general procedure B. The reaction was purified by silica gel chromatography (gradient, hexane→8% EtOAc-hexane) to yield 3-[(4-Benzoyl-thiazol-2-yl)-cyclopentyl-amino]-propionic acid tert-butyl ester (4.0 g).

Workup

  1. customthe volatiles were removed

Sources & evidence

ORD record
ord-30e2f59e678a469e8244bd7f2283a219
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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