2-hydroxy-6-iodobenzaldehyde synthesis

5synthesis methods

Product Name:2-hydroxy-6-iodobenzaldehyde
CAS Number:38169-97-0
Molecular formula:C7H5IO2
Molecular Weight:248.02

5025-59-2
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38169-97-0
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Yield:38169-97-0 93%

Reaction Conditions:

with boron tribromide in dichloromethane at -78 - 20; for 3 h;Inert atmosphere;

Steps:

29 2-Hydroxy-6-iodobenzaldehyde L29

Compound L28 (5 g, 19.1 mmol, 1 eq.) was dissolved in dry dichloromethane (200 ml) under an argon atmosphere. The solution was cooled to -78 °C and a solution of boron tribromide (95 ml of 1M in dichloromethane, 95.5 mmol, 5 eq.) was added and the mixture was stirred at room temperature until full conversion was achieved (ca. 3 hours). The mixture was cooled to -15 °C and the reaction was slowly quenched by a saturated aqueous solution of NaHCO3. The mixture was extracted with chloroform (3x), washed with brine (1x), dried with MgSO4, filtered and evaporated. The solid was adsorbed on silica gel in a mixture of cyclohexane/acetone and it was purified by flash column chromatography on silica gel (cyclohexane to 10% ethyl acetate modified with 10% methanol (v/vi)), yielded 4.4 g (93%) of the title compound as a white-off solid. 1H NMR (401 MHz, DMSO-d6) δ 11.58 (s, 1H), 10.02 (s, 1H), 7.52 (dd, J= 7.7, 1.0 Hz, 1H), 7.22 (dd, J= 8.4, 7.7 Hz, 1H), 7.00 (dd, J= 8.4, 1.1 Hz, 1H). 13CNMR(101 MHZ, DMSO-d6) δ 198.92, 162.10, 137.58, 131.87, 120.06, 118.14, 101.00. MS (ESI-QMS) m/z: [M + H]+ calcd for C7H6I02, 248.9; found, 248.9.

References:

WO2021/83438,2021,A1 Location in patent:Page/Page column 26-27

67-66-3 Synthesis