3-Chloro-5-hydroxybenzonitrile

white powder

A 250 mL flask was charged with 24b (7.0 g, 41.766 mmol) and 2, 4, 6-collidine (100 mL). The mixture was heated to 170° C. and Lil (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When 24b was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (NaA 250 mL flask was charged with R-3b (7.0 g, 41.766 mmol) and 2, 4, 6-collidine (100 mL). The mixture was heated to 170° C., LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When R-3b was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (Nastep 2-A 250 mL flask was charged with 5-chloro-3-methoxy-benzonitrile (7.0 g, 41.766 mmol) and 2, 4, 6-collidine (100 μL). A 250 mL flask was charged with 5-chloro-3-methoxy-benzonitrile (7.0 g, 41.766 mmol) and 2, 4, 6-collidine (100 mL). The mixture was heated to 170° C. and LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When R-3b was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (Nastep 2-A 250 mL flask was charged with R-3b (7.0 g, 41.766 mmol) and 2, 4, 6-collidine (100 mL). The mixture was heated to 170° C. and LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When R-3b was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (Na250 mL flask was charged with 5-chloro-3-methoxy-benzonitrile (7.O g, Al .166 mmol) and 2, 4, 6-collidine (100 mL). The mixture was heated to 170° C and LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When the methyl ether was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (NaA 250 mL round bottom flask was charged with 43 (4.2 g; 25.05 mmol) and 2, 4, 6-collidine (60 mL) was added. The mixture was stirred under an argon atmosphere until the solution was homogeneous. Anhydrous lithium iodide (10.06 g; 75.18 mmol) was added and the mixture was heated to 175° C. for 3 h. The reaction mixture was cooled to RT and partitioned between 10percent HCl and EtOAc. The EtOAc phase was washed sequentially with 10percent HCl and brine, dried (NaStep 2 3-Chloro-5-methoxybenzonitrile (46.48 g, 277.4 mmol) and anhydrous lithium iodide (60.77 g, 454.4 mmol) were suspended in anhydrous 2, 4, 6-collidine (200 ml.) and heated at 185 °C for 8 h under dry nitrogen. Upon cooling to rt, the reaction mixture solidified. The solid was broken up and poured onto a slurry of 10percent HCI and ice with additional concentrated HCI added to acidify the mixture. This mixture was extracted with EtOAc (3 x 200 ml_), the organic phases combined, dried over magnesium sulfate, filtered and concentrated to dryness. The resultant solid was triturated in a mixture of hexanes and EtOAc and filtered to afford an off-white solid. A second crop of product was obtained from the filtrate. The two portions were combined and dried under vacuum to afford the title compound (32.40 g, 76percent). 3-Chloro-5-methoxybenzonitrile (46.48 g, 277.4 mmol) and anhydrous lithium iodide (60.77 g, 454.4 mmol) were suspended in anhydrous 2, 4, 6-collidine (200 ml.) and heated at 185 3-Chloro-5-(methyloxy)benzonitrile (46.48 g, 277 mmol) and anhydrous LiI (60.77 g, 454.4 mmol) were suspended in anhydrous 2, 4, 6-collidine (200 mL) under nitrogen and heated to 185

Molecular Weight:153.56
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:152.9981414
Monoisotopic Mass:152.9981414
Topological Polar Surface Area:44
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes