ChemicalBook CAS DataBase List 2-Bromo-4-chlorophenol

2-Bromo-4-chlorophenol synthesis

5synthesis methods

Product Name:2-Bromo-4-chlorophenol
CAS Number:695-96-5
Molecular formula:C6H4BrClO
Molecular Weight:207.45

17005-59-3

695-96-5

The general procedure for the synthesis of 2-bromo-4-chlorophenol from the compound (CAS:17005-59-3) is as follows: in a 10 mL round-bottomed flask with a magnetic stir bar, phenols or olefins (0.1 mmol), carbon tetrabromide (CBr4, 33 mg, 0.1 mmol), anhydrous acetonitrile (CH3CN, 1 mL), and dichloro tris(2,2'-) bipyridine)ruthenium(II) (Ru(bpy)3Cl2, 3.8 mg, 0.005 mmol). The reaction mixture was irradiated at room temperature using a blue LED lamp (1 W) and air was continuously passed until the complete disappearance of the raw material was shown by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed by distillation under reduced pressure. Finally, the residue was purified by fast column chromatography to obtain the target product 2-bromo-4-chlorophenol.

95-56-7 Synthesis

95-56-7
311 suppliers
$9.00/5 g

695-96-5
275 suppliers
$7.00/5g

2040-88-2 Synthesis

2040-88-2
107 suppliers
$10.00/250mg

Yield:695-96-5 86%

Reaction Conditions:

Stage #1:2-hydroxybromobenzene with sulfuric acid in acetonitrile at 20; for 0.0833333 h;
Stage #2: with N-chloro-succinimide in acetonitrile at 20; for 3 h;regioselective reaction;Reagent/catalyst;

Steps:

Representative procedure for the preparation of compound 11a
General procedure: To a solution of phenol (470.6 mg, 5 mmol) in MeCN (10 mL) was added con. H2SO4 (285 μL, 1.05 equiv.) at room temperature, the mixture was stirred for 5 min. Then, NBS (934.4 mg, 1.05 equiv.) was added to the mixture. The reaction was monitored using TLC analysis. The mixture was evaporated to dryness. H2O (15 mL) was added to the residue and extracted with CH2Cl2 (3 x 15 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afford the crude product. The major product was isolated using silica gel chromatography to obtain the product as light yellow liquid; yield: 79% (0.69 g).

References:

Wu, Yong-Qi;Lu, Hai-Jia;Zhao, Wen-Ting;Zhao, Hong-Yi;Lin, Zi-Yun;Zhang, Dong-Feng;Huang, Hai-Hong [Synthetic Communications,2020,vol. 50,# 6,p. 813 - 822] Location in patent:supporting information

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