ChemicalBook CAS DataBase List 3-Iodo-4-hydroxybenzaldehyde

3-Iodo-4-hydroxybenzaldehyde synthesis

7synthesis methods

Product Name:3-Iodo-4-hydroxybenzaldehyde
CAS Number:60032-63-5
Molecular formula:C7H5IO2
Molecular Weight:248.02

123-08-0

60032-63-5

General procedure for the synthesis of 4-hydroxy-3-iodobenzaldehyde from 4-hydroxybenzaldehyde: To a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in acetic acid (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at room temperature for 16 hours and then filtered. The filtrate was poured into water (100 mL) and ethyl acetate (50 mL) was added. The aqueous phase was separated and then extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with water (2 × 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (2.0 g, 50% yield) as a white solid, which was ready to be used without further purification.LCMS (ES-) m/z 247.1 ([M-H]-) with a retention time of 1.44 min (Method 9).

2314-37-6 Synthesis

2314-37-6
100 suppliers
$17.00/250mg

60032-63-5
142 suppliers
$21.00/100mg

Yield:60032-63-5 46%

Reaction Conditions:

with boron tribromide in dichloromethane at 0 - 20; for 24 h;

Steps:

Synthesis of 4-Hydroxy-3-Iodobenzaldehyde
Approximately 1 g of 3-iodo-4-methoxybenzaldehyde was added to 100 mL of anhydrous dichloromethane and stirred at 0° C. 0.405 mL of boron tribromide was added dropwise to the solution and was allowed to warm to room temperature over a period of 24 hours. Approximately 40 mL of water was then added to the solution to quench the reaction. The aqueous and organic layers were then separated and the aqueous layer was extracted with two 100 mL washings of ethyl acetate. The ethyl acetate layers were collected and combined with the organic layer from the initial separation. The combined organic layer was washed with 100 mL of water and 100 mL of brine and was then dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. Thin layer chromatography was then applied to the crude product to determine the conditions for optimal separation by silica gel flash column chromatography. A mobile phase composition of 80% hexanes and 20% ethyl acetate provided the best separation of product from starting material. Fractions collected from the column which contained the product compound were combined and concentrated under vacuum. The final yield of purified product was approximately 46%. FIG. 3 and FIG. 4 show the respective proton NMR spectrum and MALDI MS of the synthesized 4-hydroxy-3-iodobenzaldehyde. ¹H NMR (400 MHz, CDCl₃) δ 9.81 (s, 1H), 8.22 (s, 1H), 7.80 (d, J=6.8 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 5.84 (s, 1H). MALDI MS (M+H⁺) m/z 248.238.

References:

Board of Trustees of Southern IIIinois University;Kirmess, Kristopher M.;KINSEL, Gary R.;PLUNKETT, Kyle Newton US2019/161438, 2019, A1 Location in patent:Paragraph 0077

FullText

123-08-0 Synthesis

123-08-0
952 suppliers
$5.00/10g

60032-63-5
142 suppliers
$21.00/100mg

References

67-66-3 Synthesis