ChemicalBook CAS DataBase List 4-Bromophenylacetic acid

4-Bromophenylacetic acid synthesis

13synthesis methods

Product Name:4-Bromophenylacetic acid
CAS Number:1878-68-8
Molecular formula:C8H7BrO2
Molecular Weight:215.04

4-Bromophenylacetic acid can be used as a sensitive reagent for the determination of zirconium and the separation of zirconium from titanium, iron, aluminum, copper and other metals. It can be synthesized by the hydrolysis of ethyl p-bromophenylacetate.

14062-25-0 Synthesis

14062-25-0
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1878-68-8
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Yield:1878-68-8 93%

Reaction Conditions:

with water;sodium hydroxide in 1,4-dioxane; pH=10 - 14 at 60; for 2 h;

Steps:

19 Preparation of p-Bromophenylacetic Acid from p-Bromotoluene and Ethanol
p-Bromotoluene (2.72 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl₂(3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 89 mg ethyl p-bromoacetate was obtained by column chromatography, in a yield of 73%. ¹HNMR (400 MHz, CDCl₃) δ 1.23 (t, J=7.2 Hz, 3H), 3.56 (s, 2H), 4.12 (q, J=6.8 Hz, 2H), 7.15-7.17 (m, 2H), 7.43-7.45 (m, 2H); ¹³CNMR (100 MHz, CDCl₃) δ 14.2, 40.8, 61.0, 121.1, 131.0, 131.6, 133.1, 171.1; HRMS (ESI) calcd. for C₁₀H₁₁BrNaO₂[M+Na]: 264.9835. found: 264.9837. The ethyl p-bromophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 73 mg product p-bromophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

References:

Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences;Huang, Hanmin;Xia, Chungu;Xie, Pan US2013/303798, 2013, A1 Location in patent:Paragraph 0018; 0064; 0065

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201230-82-2 Synthesis