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

Temperatur

80 °C

m-Tolylacetic acid (4.0 g, 26.64 mmol) and AIBN (α,α′-azobisisobutyronitrile) (0.044 g, 0.266 mmol) were dissolved in acetonitrile (11.9 g) and the solution was raised to 80° C. To this solution was dropped a solution of N-bromosuccinimide (4.98 g, 27.97 mmol) and AIBN (α,α′-azobisisobutyronitrile) (0.044 g, 0.266 mmol) in acetonitrile (32 g) for 1.5 hours. After stirring for 30 minutes the mixture was cooled to 50° C. and thereto was added butyl acetate (38.7 g). The mixture was concentrated to remove only acetonitrile. The resulting succinimide (crystal) was removed and the residue was washed three times with water. After concentrating to a desired concentration, thereto was added at 45° C. n-heptane (45.6 g) to produce a crystal. After cooling to 5° C., the crystal was filtered to give the sub-subject compound (3.76 g) as a white crystal. Yield: 62%

1. temperaturewas cooled to 50° C.
2. concentrationThe mixture was concentrated
3. customto remove only acetonitrile
4. customThe resulting succinimide (crystal) was removed
5. washthe residue was washed three times with water
6. concentrationAfter concentrating to a desired
7. concentrationconcentration
8. additionwas added at 45° C. n-heptane (45.6 g)
9. customto produce a crystal
10. temperatureAfter cooling to 5° C.
11. filtrationthe crystal was filtered

ORD-Eintrag

ord-ade5897b345543b285e6b2c822ac0749

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08865896B2