ChemicalBook CAS DataBase List 2,2-DIBROMO-1-P-TOLYLETHANONE

2,2-DIBROMO-1-P-TOLYLETHANONE synthesis

13synthesis methods

Product Name:2,2-DIBROMO-1-P-TOLYLETHANONE
CAS Number:13664-98-7
Molecular formula:C9H8Br2O
Molecular Weight:291.97

766-97-2 Synthesis

766-97-2
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13664-98-7
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Yield:13664-98-7 97%

Reaction Conditions:

with Oxone;potassium bromide in water;acetonitrile at 20; for 0.25 h;

Steps:

typical procedure for preparation of a,a-dichloroketons and a,a-dibromoketones

General procedure: 1-Ethynyl-4-methylbenzene 1b (0.5 g, 4.3 mmol), KBr (1.0 g, 8.6 mmol),oxone (5.3 g, 8.6 mmol), and acetonitrile (10 mL) were taken into a 100 mL round bottomed flask and stirred at room temperature.Next, water (5 mL) was added dropwise to the mixture. With the addition of water,exothermicreaction was observed and temperature of the reaction mixture increased to 50 C. After completion of the reaction (TLC), reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3 15 mL). The combinedorganic layers were washed with brine, dried over anhyd. Na2SO4, andconcentrated under reduced pressure. Purification of the crude product bynormal column chromatography (silica gel 60-120 mesh, n-hexane) furnished2,2-dibromo-1-p-tolylethanone 3b (1.22 g, 97%) as a pale yellow solid (mp 96-98 C; lit.22 97-99 C), which was characterized by the following spectral data:1H NMR (300 MHz, CDCl3): d = 7.98 (d, J = 8.3 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H),6.69 (s, 1H), 2.44 (s, 3H); 13C NMR (75 MHz, CDCl3): d = 185.5, 145.6, 129.7,129.5, 128.0, 39.9, 21.7; IR (neat): t 3012, 2932, 1708, 1423, 1282, 993, 748,682 cm1; Elemental Analysis: C, 37.14; H, 2.775%; Calcd: C, 37.04; H, 2.76%.

References:

Madabhushi, Sridhar;Jillella, Raveendra;Mallu, Kishore Kumar Reddy;Godala, Kondal Reddy;Vangipuram, Venkata Sairam [Tetrahedron Letters,2013,vol. 54,# 30,p. 3993 - 3996] Location in patent:supporting information

122-00-9 Synthesis