ChemicalBook CAS DataBase List 2-(Bromomethyl)benzoic acid

2-(Bromomethyl)benzoic acid synthesis

4synthesis methods

Product Name:2-(Bromomethyl)benzoic acid
CAS Number:7115-89-1
Molecular formula:C8H7BrO2
Molecular Weight:215.04

118-90-1 Synthesis

118-90-1
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7115-89-1
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$14.14/250mgs:

Yield:7115-89-1 84%

Reaction Conditions:

with bromine in tetrachloromethane;Heating / reflux;UV-irradiation;

Steps:

11 2-Bromomethylbenzoic acid

2-Bromomethylbenzoic acid A solution of o-Toluic acid (15.0 g, 110.3 mmol) in CCl₄ (150 mL) was warmed to reflux and treated with a solution of Br₂ (17.6 g, 110.3 mmol) in CCl₄ (150 mL) whilst irradiating the solution with a 200 W tungsten lamp. Bromine addition was such that a pale orange color was observed throughout the addition. A vigorous reflux and evolution of hydrogen bromide was also observed during addition. At the end of the addition a colorless suspension was observed and heating and irradiation were continued for a further 5 minutes before being removed. TLC analysis [hexane/EtOAc (1:1)] of the mixture indicated that no starting material remained. The solution was cooled to 65° C. and treated with n-hexane then further cooled to room temperature. The precipitated solid was removed by filtration and washed with n-hexane and dried in a vacuum oven at 40° C. (-30 inHg). This provided the desired 2-Bromomethylbenzoic acid as a colorless solid (20. 0 g, 84%), which was deemed pure enough (NMR analysis) for use in subsequent steps without the need for further purification.

References:

US2005/288283,2005,A1 Location in patent:Page/Page column 5; 6

87-41-2 Synthesis