ChemicalBook CAS DataBase List 5-bromo-2-chloro-4’-ethoxydiphenylmethane

5-bromo-2-chloro-4’-ethoxydiphenylmethane synthesis

13synthesis methods

Product Name:5-bromo-2-chloro-4’-ethoxydiphenylmethane
CAS Number:461432-23-5
Molecular formula:C15H14BrClO
Molecular Weight:325.63

461432-22-4 Synthesis

(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

461432-22-4
326 suppliers
$5.00/250mg

5-bromo-2-chloro-4’-ethoxydiphenylmethane

461432-23-5
486 suppliers
$30.00/1g

Yield:461432-23-5 97%

Reaction Conditions:

with triethylsilane;boron trifluoride diethyl ether complex in 1,2-dichloro-ethane;acetonitrile at 0 - 50; for 3 h;

Steps:

12 4.12. 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene (15)

Et₃SiH (6.76?mL, 42.34?mmol) was added to a solution of compound 14 (6.0?g, 17.8?mmol) in 1:2 mixture of dry 1,2-dichloroethane/acetonitrile (2:1, 60?mL) and the mixture was cooled in an ice bath. BF₃·OEt₂ (2.53?mL, 20.51?mmol) was added and the mixture was heated at 50?°C for 3?h and then cooled at room temperature. Aqueous 7N KOH (30?mL) was added and the aqueous layer was extracted with dichloromethane (2?*?100?mL). The combined organic layers were washed with 2N KOH (2*) and brine and dried over Na₂SO₄. The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column (hexane/ethyl acetate 15:1) to give product 15 (5.6?g, 97%) as colorless crystals, with spectral and physical data identical to those reported in the literature [7], m.p. 40-42 °C (lit. m.p. 37 °C and 40-41 °C). ¹H NMR (400 MHz, CDCl₃) 7.20-7.28 (m, 3H), 7.08 (d, J = 8.8, 2H), 6.83 (d, J = 8.8, 2H), 4.00 (q, J = 7.0, 2H), 3.96 (s, 2H), 1.40 (t, J = 7.0, 3H); ¹³C NMR (125 MHz, CDCl₃) 157.6, 141.3, 133.5, 133.1, 130.9, 130.5, 130.4, 130.0, 120.4, 114.6, 63.4, 38.2, 14.9. LC-MS (ESI positive) m/z: 325 [M+H]⁺.

References:

Triantakonstanti, Virginia V.;Mountanea, Olga G.;Papoulidou, Kyriaki-Eleni C.;Andreou, Thanos;Koftis, Theocharis V.;Gallos, John K. [Tetrahedron,2018,vol. 74,# 39,p. 5700 - 5708]

864070-18-8 Synthesis