m-Tolylacetic acid → 2-(3-(Bromomethyl)phenyl)acetic acid

To a solution of m-tolylacetic acid (25.00 g, 166.5 mmol) in anhydrous carbon tetrachloride (200 ml) was added N-bromosuccinimide (30.00 g, 168.6 mmol), and the mixture was gradually heated to the boiling point. After heating the mixture under reflux for 5.5 hr, the reaction mixture was cooled to room temperature, the insoluble material was removed by filtration and washed twice with carbon tetrachloride (100 ml). The filtrate was concentrated, carbon tetrachloride (60 ml) was added and the residue was dissolved by heating at about 70° C. The solution was cooled to about 40° C., and hexane (300 ml) was added dropwise. After stirring at room temperature for 30 min, the precipitated crystals were filtered, washed with hexane and dried under reduced pressure to give (3-bromomethylphenyl)acetic acid (22.80 g, 99.53 mmol, yield 59.8%) as a white solid.

1. temperaturethe mixture was gradually heated to the boiling point
2. temperatureAfter heating the mixture
3. temperatureunder reflux for 5.5 hr
4. customthe insoluble material was removed by filtration
5. washwashed twice with carbon tetrachloride (100 ml)
6. concentrationThe filtrate was concentrated
7. additioncarbon tetrachloride (60 ml) was added
8. dissolutionthe residue was dissolved
9. temperatureby heating at about 70° C
10. temperatureThe solution was cooled to about 40° C.
11. additionhexane (300 ml) was added dropwise
12. filtrationthe precipitated crystals were filtered
13. washwashed with hexane
14. customdried under reduced pressure

ORD record

ord-80dcf63d419e4703b9cca8953810fd2c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2