background and overview[1]
3-(3-iodo)phenylacetic acid can be used as a pharmaceutical synthesis intermediate. if 3-(3-iodo)phenylacetic acid is inhaled, move the patient to fresh air; if the skin comes in contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel uncomfortable; if the eye contact if exposed to sunlight, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
preparation[1]
the preparation of (3-iodo)phenylacetic acid is as follows:
the specific steps are as follows: stir into a stirred solution of (3-aminophenyl)propionic acid (4.91g, 29.7mmol) in water (50ml) and concentrated h2so4 (4ml) at -7°c. add a solution of nano2 (2.4g, 34.7mmol) in a minimum amount of water to the (ice-salt bath) to drain the nitrite solution below the surface of the solution and maintain the temperature below 0°c. after 10 minutes, use starch-ki indicator paper to check whether there is excess no2- in the mixture to ensure that the diazotization is complete. add diethyl ether (50 ml), then slowly add a solution of ki (15 g, 90 mmol) in a minimum amount of water to control the violent evolution of n2. after the addition was complete, the reaction was stirred and allowed to warm to ambient temperature over 3 hours. the layers were separated and the aqueous layer was extracted with additional diethyl ether (2 x 50 ml). the combined ether layers were back-extracted with 5% (w/v) nahso3 (aqueous solution), brine (1 × 25 ml), dried over mgso4, filtered and concentrated to obtain (3-iodo)phenylacetic acid, yield 8.0 g.
1hnmr (300mhz, d6-dmso) δ12.13 (bs, 11h), 7.62 (d, 1h, j=1.7hz), 7.55 (dd, 1h, j=1.4,6.4hz), 7.26 (d, 1h, j=7.4hz), 7.09 (t, 1h, j=7.6hz), 2.78 (t, 3h, j=7.6hz), 2.53 (t, 3h, j=7.5hz); ms (esi) m/ z275(m-h).
main reference materials
[1] u.s. pat. appl. publ., 20040167188, 26 aug 2004
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