methyl 3,5-dihydroxy-4-iodobenzoate synthesis
- Product Name:methyl 3,5-dihydroxy-4-iodobenzoate
- CAS Number:338454-02-7
- Molecular formula:C8H7IO4
- Molecular Weight:294.04
2150-44-9
338454-02-7
Methyl 3,5-dihydroxybenzoate (4-1) (5.0 g, 30 mmol) was used as a raw material, which was dissolved in a solvent mixture of methanol (70 mL) and NaHCO3 aqueous solution (70 mL, 1 M) at 0 °C. Aqueous potassium iodide solution (10 mL, 3.8 M) of iodine (7.4 g, 29.3 mmol) was slowly added via syringe pump (12 mL/min). After 1 h of reaction, the reaction solution was acidified to pH 2 with 37% HCl and then gradually warmed up to room temperature. The reaction mixture was concentrated to dryness and the product was purified by recrystallization from methanol-water system. Methyl 3,5-dihydroxy-4-iodobenzoate (4-2) in yellow crystalline form was finally obtained (4.4 g, 14.8 mmol, 49% yield).LCMS analysis: calculated value 293.94, measured value 293.03 (M-).
67-56-1
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Yield: 90%
Reaction Conditions:
with sulfuric acid at 60; for 3.75 h;
Steps:
1.b Stage b) 3,5-Dihydroxy-4-iodo-benzoic acid methyl ester
3,5-Dihydroxy-4-iodo-benzoic acid (810 g; 2.89 mol) is dissolved in methanol (3,800 ml), while stirring and gassing with argon, sulphuric acid (57.5 ml) is cautiously added and the mixture is heated to 60° C. After 3 hours at this temperature, sulphuric acid (12 ml) is added again and stirring is continued for 45 minutes. After removal of the heating bath water (5,000 ml) is cautiously added and the mixture is cooled to 0° C. The crystals which have precipitated out are then filtered off with suction, washed with ice-water (2*500 ml) and dried under a high vacuum. Yield: 772 g (90%) as white crystals. M.p. 222-223° C. MS: 294 (M); 263 (M-OCH3)
References:
Basilea Pharmaceutica AG US6821980, 2004, B1 Location in patent:Page column 21
2150-44-9
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$5.00/5g
338454-02-7
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$53.00/100mg
99-10-5
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338454-02-7
56 suppliers
$53.00/100mg