ChemicalBook CAS DataBase List 2-Bromo-2-phenylacetic acid

2-Bromo-2-phenylacetic acid synthesis

8synthesis methods

Product Name:2-Bromo-2-phenylacetic acid
CAS Number:4870-65-9
Molecular formula:C8H7BrO2
Molecular Weight:215.04

103-82-2

4870-65-9

General procedure for the synthesis of α-bromophenylacetic acid from phenylacetic acid: 2-phenylacetic acid (376 mg, 2.7 mmol), N-bromosuccinimide (540 mg, 3.05 mmol), and carbon tetrachloride (5.5 mL) were added to a dry two-necked flask fitted with a condensing unit. Azobisisobutyronitrile (23 mg, 0.14 mmol) was added with stirring and the reaction was heated to reflux at 77°C with stirring for 2 hours. The progress of the reaction was monitored by nuclear magnetic resonance spectroscopy (1H NMR) until 2-phenylacetic acid was completely consumed. Upon completion of the reaction, the reaction was cooled naturally to room temperature, and the reaction mixture was diluted with hexane (10.0 mL) and filtered. The solvent was removed by rotary evaporation and purified by silica gel column chromatography (eluent: n-hexane/ether, 2:1, v/v) to afford α-bromophenylacetic acid as a white solid (95% yield).

103-82-2
0 suppliers
$22.19/5g

4870-65-9
195 suppliers
$8.00/1g

Yield:4870-65-9 95%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 77; for 2 h;

Steps:

1.1 (1) compound1a synthesis:
30.0 ml dry two neck bottles and a condensation device, adding 2-phenyl acetic acid (376 mg, 2 . 77mmol), N-bromo succinimide (540 mg, 3 . 05mmol) and carbon tetrachloride (5.5 ml), stirring, add azodiisobutanenitrile (23 mg, 0 . 14mmol), 77 °C heating to reflux, the reaction under stirring 2 hours, by nuclear magnetic resonance spectral (¹HNMR) monitoring reaction 2-phenyl acetic acid dematerialised, natural cooling to room temperature, the normal hexane (10.0 ml) in two neck bottle to dilute and to filter and, revolving off a solvent, a silica gel column (eluent: n-hexane and ethyl ether volume ratio [...] 2 1) to obtain white solid 2-bromo-2-benzoic acid1a (95% yield).

References:

Henan University;Jiang, Zhiyong;Zhu, Bo;Zhao, Xiaowei;Jiao, Lihui;Li, Jiangtao CN105384703, 2016, A Location in patent:Paragraph 0014

FullText

2835-06-5 Synthesis