4-Bromobenzophenone → (4-Bromophenyl)(hydroxy)phenylacetic acid

Zinc iodide (0.5 g) was added to a stirring solution of 4-bromobenzophenone (54.81 g, 0.21 mol) in dry dichloromethane (500 ml) at room temperature under N2 atmosphere. Trimethylsilyl cyanide (25 g, 0.25 mol) was added dropwise from an addition flask over a period of 1 hour and the mixture stirred at room temperature for 72 hours. The reaction mixture was treated with saturated sodium bicarbonate (200 ml) and stirred for 1 hour. The organic layer was separated, washed with water (2×150 ml) and concentrated. The residue was suspended in H2O:HCl:AcOH (1:33; 500 ml) and heated at 85°-90° C. for 48 hours. The solution was concentrated under vacuum to about 100 ml and treated with saturated sodium bicarbonate (400 ml) and extracted with ether (3×100 ml). The aqueous layer was acidified with 6N hydrochloric acid and the separated solid was dissolved in ether (300 ml). This organic layer was washed with water, filtered and the filtrate was evaporated to provide a colorless crystalline solid of (RS)-4-bromobenzilic acid in 19% yield (12 g); mp 125°-126° C.; TLC [silica gel, toluene-acetic acid] Rf 0.32; 1H NMR (DMSO-d6) δ2.38 (bs, 2H, COOH and OH) and 7.38-7.70 (m, 9H, AR-H).

1. stirringstirred for 1 hour
2. customThe organic layer was separated
3. washwashed with water (2×150 ml)
4. concentrationconcentrated
5. temperatureheated at 85°-90° C. for 48 hours
6. concentrationThe solution was concentrated under vacuum to about 100 ml
7. additiontreated with saturated sodium bicarbonate (400 ml)
8. extractionextracted with ether (3×100 ml)
9. dissolutionthe separated solid was dissolved in ether (300 ml)
10. washThis organic layer was washed with water
11. filtrationfiltered
12. customthe filtrate was evaporated

ORDレコード

ord-6503c320498a4dc8a83651f6414d1b40

出典データセット

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05387409