No renderable structure data available
COC(=O)C1=CC(=C(C(=C1)I)O)IChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | Methyl 4-hydroxy-3,5-diiodobenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 3337-66-4 |
| Database ID | 12207035 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
Methyl 4-hydroxy-3,5-diiodobenzoate (CAS 3337-66-4) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 12207035
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-474c341784d2416b9b959d43974c232aConditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of phenylboronic acid (4.95 g, 40.57 mmol), Ba(OH)2.H2O (10.48 g, 55.33 mmol), and Pd(OAc)2 (0.414 g, 1.84 mmol) in DME/H2O (110 mL/20 mL) was added 3,5-diiodo-4-hydroxybenzoic acid methyl ester (7.45 g, 18.44 mmol). The mixture was stirred at 85° C. for 3 h and was then cooled and concentrated. The residue was partitioned between ethyl acetate/2N HCl. The organic phase was dried (MgSO4) and concentrated to give a solid which was triturated with diethyl ether/petroleum ether to give 3.51 g (62.5%) of product as a white solid. 1H NMR (DMSO-d6) δ9.27 (s, 1H), 7.27 (s, 2H), 7.25-7.40 (m, 10H), 3.81 (s, 3H). was then cooled concentrated The residue was partitioned between ethyl acetate/2N HCl The organic phase was dried (MgSO4) concentrated to give a solid which was triturated with diethyl ether/petroleum ether
Source ID: ord-ed7a42382f5243289902d150a2040f0aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 3,5-diiodo-4-hydroxybenzoic acid (10.00 g, 25.65 mmol) in dry methanol (250 mL) was added TiCl4 (1.41 mL, 12.82 mmol) in one lot. The reaction was stirred at reflux for 6 h and was then stirred at room temperature for 24 h. The mixture was concentrated down and the residue was taken up in diethyl ether and filtered through a plug of silica gel. The filtrate was concentrated down and the residue was recrystallized from hot methanol to give 7.84 g (76%) of the ester as white crystalline needles. 1H NMR (DMSO-d6) δ10.41 (br s, 1H), 8.22 (s, 2H), 3.79 (s, 3H). at reflux for 6 h was then stirred at room temperature for 24 h The mixture was concentrated down filtered through a plug of silica gel The filtrate was concentrated down the residue was recrystallized from hot methanol
Source ID: ord-d88a9bb3312640a8a89ef04c966aff67Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Methyl 4-hydroxy-3,5-diiodobenzoate (D254) was prepared in an analogous manner to Description 25 (D25) from commercially available 4-hydroxy-3,5-diiodobenzoic acid.
Source ID: ord-45cb3009486240a59bb49fe6b5e5a426Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of phenylboronic acid (4.95 g, 40.57 mmol), Ba(OH)2.H2O (10.48 g, 55.33 mmol), and Pd(OAc)2 (0.414 g, 1.84 mmol) in DME/H2O (110 mL/20 mL) was added 3,5-diiodo-4-hydroxybenzoic acid methyl ester (7.45 g, 18.44 mmol). The mixture was stirred at 85° C. for 3 h and was then cooled and concentrated. The residue was partitioned between ethyl acetate/2N HCl. The organic phase was dried (MgSO4) and concentrated to give a solid which was triturated with diethyl ether/petroleum ether to give 3.51 g (62.5%) of product as a white solid. 1H NMR (DMSO-d6) δ9.27 (s, 1H), 7.27 (s, 2H), 7.25-7.40 (m, 10H), 3.81 (s, 3H). was then cooled concentrated The residue was partitioned between ethyl acetate/2N HCl The organic phase was dried (MgSO4) concentrated to give a solid which was triturated with diethyl ether/petroleum ether
Source ID: ord-ed7a42382f5243289902d150a2040f0aConditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of phenylboronic acid (4.95 g, 40.57 mmol), Ba(OH)2.H2O (10.48 g, 55.33 mmol), and Pd(OAc)2 (0.414 g, 1.84 mmol) in DME/H2O (110 mL/20 mL) was added 3,5-diiodo-4-hydroxybenzoic acid methyl ester (7.45 g, 18.44 mmol). The mixture was stirred at 85° C. for 3 h and was then cooled and concentrated. The residue was partitioned between ethyl acetate/2N HCl. The organic phase was dried (MgSO4) and concentrated to give a solid which was triturated with diethyl ether/petroleum ether to give 3.51 g (62.5%) of product as a white solid. 1H NMR (DMSO-d6) δ9.27 (s, 1H), 7.27 (s, 2H), 7.25-7.40 (m, 10H), 3.81 (s, 3H). was then cooled concentrated The residue was partitioned between ethyl acetate/2N HCl The organic phase was dried (MgSO4) concentrated to give a solid which was triturated with diethyl ether/petroleum ether
Source ID: ord-ed7a42382f5243289902d150a2040f0aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 3,5-diiodo-4-hydroxybenzoic acid (10.00 g, 25.65 mmol) in dry methanol (250 mL) was added TiCl4 (1.41 mL, 12.82 mmol) in one lot. The reaction was stirred at reflux for 6 h and was then stirred at room temperature for 24 h. The mixture was concentrated down and the residue was taken up in diethyl ether and filtered through a plug of silica gel. The filtrate was concentrated down and the residue was recrystallized from hot methanol to give 7.84 g (76%) of the ester as white crystalline needles. 1H NMR (DMSO-d6) δ10.41 (br s, 1H), 8.22 (s, 2H), 3.79 (s, 3H). at reflux for 6 h was then stirred at room temperature for 24 h The mixture was concentrated down filtered through a plug of silica gel The filtrate was concentrated down the residue was recrystallized from hot methanol
Source ID: ord-d88a9bb3312640a8a89ef04c966aff67Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 3,5-diiodo-4-hydroxybenzoic acid (10.00 g, 25.65 mmol) in dry methanol (250 mL) was added TiCl4 (1.41 mL, 12.82 mmol) in one lot. The reaction was stirred at reflux for 6 h and was then stirred at room temperature for 24 h. The mixture was concentrated down and the residue was taken up in diethyl ether and filtered through a plug of silica gel. The filtrate was concentrated down and the residue was recrystallized from hot methanol to give 7.84 g (76%) of the ester as white crystalline needles. 1H NMR (DMSO-d6) δ10.41 (br s, 1H), 8.22 (s, 2H), 3.79 (s, 3H). at reflux for 6 h was then stirred at room temperature for 24 h The mixture was concentrated down filtered through a plug of silica gel The filtrate was concentrated down the residue was recrystallized from hot methanol
Source ID: ord-d88a9bb3312640a8a89ef04c966aff67Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-474c341784d2416b9b959d43974c232aPubChem References
These sources are listed in the compound's public database record.
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