Hydrochloric Acid → Methyl 4-bromo-2-chlorobenzeneacetate

Temperature

0 °C

(4-Bromo-2-chloro-phenyl)-acetonitrile (1.98 g, 8.6 mmoles) was dissolved into MeOH (50 mL) and water (5 mL), and the resulting homogeneous mixture was chilled to 0° C. To this stirring (cold) mixture was slowly (carefully) added concentrated HCl (25 mL). After the addition was complete the mixture was refluxed for 16 hours. After this period the reaction mixture was combined with ice and the resulting heterogeneous mixture was extracted with diethyl ether (3×50 mL). The combined ethereal layer was washed with brine, dried over anhydrous MgSO4, and evaporated in vacuo to yield clean (4-bromo-2-chloro-phenyl)-acetic acid methyl ester (2.3 g, 80%). 1H-NMR (CDCl3): δ 7.56 (d, J=2.0 Hz, 1H), 7.37 (dd, J′=8.3 Hz, J″=2.0 Hz, 1H), 7.16 (d, J=8.3 Hz, 1H), 3.73 (s, 2H), 3.72 (s, 3H).

1. additionAfter the addition
2. temperaturewas refluxed for 16 hours
3. waitAfter this period the reaction mixture was combined with ice
4. extractionthe resulting heterogeneous mixture was extracted with diethyl ether (3×50 mL)
5. washThe combined ethereal layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. customevaporated in vacuo

ORD record

ord-3b3bc9eb3b5e403fb82369dfbe611056

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013001B2