5-BROMO-2-IODOBENZENEMETHANOL

To a solution of compound 10 (5.2 g, 0.015 mol) in dry CHTo a stirred solution of sodium borohydride (1 .1 g, 14.7 mmol, 2 equiv) in ethanol (20 mL) was added methyl 5-bromo-2-iodobenzoate in THF (10 mL) at 5°C. The reaction mixture was warmed to room temperature and stirred for 18 h under nitrogen atmosphere. Additional quantity of sodium borohydride (0.84 g, 22 mmol, 1 .5 equiv) was added and the mixture was stirred for 22 h. The reaction mixture was cooled to 0°C, treated with 10 mL of 15percent citric acid slowly. The reaction mixture was extracted with DCM (2 x 75 mL). The organic layer was washed with 15percent of aq. NaCI (100 mL), and then dried over sodium sulphate and evaporated to obtain (5-bromo-2-iodophenyl)methanol (4.5 g, 100percent) as white solid. NMR (400 MHz, CDCITo a stirred mixture of acid 2-iodo-5-bromobenzoic acid (15.0 g, 45.9 mmol) in dry THF (100 mL) under argon was added neat BH5-Bromo-2-iodobenzoic acid (7c) (750 mg, 2.3 mmol) was dissolved in dry THF (25 mL) and the reaction mixture was cooled to 0 °C. NEtThe mixture solution of 5-bromo-2-iodobenzyl bromide (16.0g, 50.0mmol), NaAc (4.9g, 60.0mmol), tetrabutylammonium bromide (1.6g, 5.0mmol), and 300mL distilled water were stirred and heated to 110°C. After refluxing for 20h, 30percent NaOH (8mL) was added into the above solution (pH value was controlled at 9–10). The reaction was continued at 110°C for 24h. A precipitate was produced when the reaction mixture was cooled. After washed with water, the crude product was purified by column chromatography on silica with as the petroleum ether/ethyl acetate (3:1) as eluent to give 12.5g of a white solid. Yield:95percent;

Molecular Weight:312.93
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:311.86467
Monoisotopic Mass:311.86467
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes