Hydrochloric Acid → Methyl 4-bromo-2-chlorobenzeneacetate

反応式

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[C:4]([Cl:11])[CH:3]=1.[CH3:12][OH:13].Cl.[OH2:15]>>[CH3:12][O:13][C:9](=[O:15])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:11]

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 962Water

HCID 58762522(4-Bromo-2-chlorophenyl)acetonitrile

生成物 1

HCID 57624630Methyl 4-bromo-2-chlorobenzeneacetate収率 80%

反応条件

温度: 0 °C

実験手順

(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).