ChemicalBook CAS DataBase List 2-Bromo-3',4'-(methylenedioxy)propiophenone

2-Bromo-3',4'-(methylenedioxy)propiophenone synthesis

3synthesis methods

Product Name:2-Bromo-3',4'-(methylenedioxy)propiophenone
CAS Number:52190-28-0
Molecular formula:C10H9BrO3
Molecular Weight:257.08

Bromine (10.0 mmol) was added to a solution of the ketone (10.0 mmol) in Et2O (25 mL). The solution was stirred for 30 min (until the color of the solution changed from red to light-yellow). Then, the reaction was quenched with water (10 mL), and the mixture was diluted with Et2O (25 mL). The organic layer was washed with a saturated solution of aqueous NaHCO3 (30 mL), a saturated solution of aqueous Na2S2O3 (30 mL), and brine (30 mL), and then it was dried over MgSO4, filtered, and concentrated. The α-bromoketone was purified by flash chromatography on silica gel. 1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one [52190-28-0]. This compound was prepared according to the General Procedure from 3,4-methylenedioxypropiophenone (1.78 g, 10.0 mmol). The product was obtained as a white solid (eluted with 50% CH2Cl2 in hexanes; 2.13 g, 82% yield). 1H NMR (CDCl3, 500 MHz) δ 7.64 (d, J= 8.0 Hz, 1H), 7.49 (s, 1H), 6.87 (d, J= 8.0 Hz, 1H), 6.07 (s, 2H), 5.21 (q, J= 7.0 Hz, 1H), 1.88 (d, J= 7.0 Hz, 3H).
1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one synthesis

1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one synthesis

28281-49-4 Synthesis

28281-49-4
158 suppliers
$89.09/5g

2-Bromo-3',4'-(methylenedioxy)propiophenone

52190-28-0
85 suppliers
$140.00/50mg

Yield:52190-28-0 87%

Reaction Conditions:

with bromine in chloroform at 0;

Steps:

4.1.8 4.1.8 1-(4-Benzyloxy-3-methoxyphenyl)-2-bromopropan-1-one (5a)

General procedure: To a solution of 4a (3.90?g, 14.4?mmol) in CHCl₃ (100?mL) was added Br₂ (741?μL, 14.4?mmol) in CHCl₃ (45.0?mL) at 0?°C. After being stirred overnight, saturated NaHCO₃ solution was added and extracted with DCM. The organic layers were dried over Na₂SO₄ and concentrated in vacuo. The residue was purified by column chromatography (hexane:EtOAc?=?88:12) to afford 5a (3.93?g, 78%) as a colorless oil.

References:

Harada, Kenichi;Zaha, Katsuyoshi;Bando, Rina;Irimaziri, Ryo;Kubo, Miwa;Koriyama, Yoshiki;Fukuyama, Yoshiyasu [European Journal of Medicinal Chemistry,2018,vol. 148,p. 86 - 94]

63740-97-6 Synthesis

63740-97-6
83 suppliers
$8.00/1g

52190-28-0
85 suppliers
$140.00/50mg

References

7451-98-1
66 suppliers
$42.32/1g

52190-28-0
85 suppliers
$140.00/50mg

References