No renderable structure data available
C1=C(C=C(C=C1Br)I)COChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (3-Bromo-5-iodophenyl)methanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 188813-08-3 |
| Database ID | 15467379 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(3-Bromo-5-iodophenyl)methanol (CAS 188813-08-3) 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 15467379
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-b01742638349494bb877ae4f5a93fdeaConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To methyl 5-bromo-3-iodobenzoate (Step A above) (5.01 g, 0.015 mole) in anhydrous methylene chloride (100 mL) at -78° C., was added dropwise minutes, diisobutylaluminum hydride (5.50 mL, 0.03 mole). The mixture was stirred for 1 hour then allowed to warm to 0° C. The reaction solution was poured into 600 mL, chilled 3N HCl and extracted 3× with methylene chloride (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield 5-bromo-3-iodobenzyl alcohol (4.54 g) as a white solid. MP=110-112° C. MS and NMR were consistent with the desired structure. The reaction solution was poured into 600 mL extracted 3× with methylene chloride (150 mL) dried over MgSO4 concentrated under vacuum
Source ID: ord-7a3136ee0bb84c16864a250cede4929fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-bromo-5-iodophenyl)methanol from the previous step (1.0 eq.) and Dess-Martin periodinane (1.18 eq.) was stirred at RT in dichloromethane (0.1 M) for 45 min. The reaction mixture was diluted with ether, filtered through a plug of SiO2, and the silica washed with a 3:1 (v/v) mixture of hexanes:EtOAc. The filtrate was concentrated in vacuo and passed again through a plug of SiO2, eluting with a 3:1 (v/v) mixture of hexanes:EtOAc to afford the title compound as a light yellow solid. filtered through a plug of SiO2 the silica washed with a 3:1 (v/v) mixture of hexanes The filtrate was concentrated in vacuo eluting with a 3:1 (v/v) mixture of hexanes
Source ID: ord-6897acc0ca1c4392a1990ff1b4fc9573Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromo-5-iodobenzoic acid (1.0 eq.) in THF (0.2 M) at RT was added borane-methyl sulfide complex (1.5 eq). After 3 days of stirring at RT, the reaction mixture was quenched cautiously with 2 N aq. HCl and extracted with ether. The combined organic extracts were washed with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil. the reaction mixture was quenched cautiously with 2 N aq. HCl extracted with ether The combined organic extracts were washed with 1 N aq. NaOH, water and brine dried over MgSO4 filtered
Source ID: ord-d1100e98bace429eb32b1bad879614ddConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To methyl 5-bromo-3-iodobenzoate (Step A above) (5.01 g, 0.015 mole) in anhydrous methylene chloride (100 mL) at -78° C., was added dropwise minutes, diisobutylaluminum hydride (5.50 mL, 0.03 mole). The mixture was stirred for 1 hour then allowed to warm to 0° C. The reaction solution was poured into 600 mL, chilled 3N HCl and extracted 3× with methylene chloride (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield 5-bromo-3-iodobenzyl alcohol (4.54 g) as a white solid. MP=110-112° C. MS and NMR were consistent with the desired structure. The reaction solution was poured into 600 mL extracted 3× with methylene chloride (150 mL) dried over MgSO4 concentrated under vacuum
Source ID: ord-7a3136ee0bb84c16864a250cede4929fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-bromo-5-iodophenyl)methanol from the previous step (1.0 eq.) and Dess-Martin periodinane (1.18 eq.) was stirred at RT in dichloromethane (0.1 M) for 45 min. The reaction mixture was diluted with ether, filtered through a plug of SiO2, and the silica washed with a 3:1 (v/v) mixture of hexanes:EtOAc. The filtrate was concentrated in vacuo and passed again through a plug of SiO2, eluting with a 3:1 (v/v) mixture of hexanes:EtOAc to afford the title compound as a light yellow solid. filtered through a plug of SiO2 the silica washed with a 3:1 (v/v) mixture of hexanes The filtrate was concentrated in vacuo eluting with a 3:1 (v/v) mixture of hexanes
Source ID: ord-6897acc0ca1c4392a1990ff1b4fc9573Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromo-5-iodobenzoic acid (1.0 eq.) in THF (0.2 M) at RT was added borane-methyl sulfide complex (1.5 eq). After 3 days of stirring at RT, the reaction mixture was quenched cautiously with 2 N aq. HCl and extracted with ether. The combined organic extracts were washed with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil. the reaction mixture was quenched cautiously with 2 N aq. HCl extracted with ether The combined organic extracts were washed with 1 N aq. NaOH, water and brine dried over MgSO4 filtered
Source ID: ord-d1100e98bace429eb32b1bad879614ddConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromo-5-iodobenzoic acid (1.0 eq.) in THF (0.2 M) at RT was added borane-methyl sulfide complex (1.5 eq). After 3 days of stirring at RT, the reaction mixture was quenched cautiously with 2 N aq. HCl and extracted with ether. The combined organic extracts were washed with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil. the reaction mixture was quenched cautiously with 2 N aq. HCl extracted with ether The combined organic extracts were washed with 1 N aq. NaOH, water and brine dried over MgSO4 filtered
Source ID: ord-d1100e98bace429eb32b1bad879614ddConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b01742638349494bb877ae4f5a93fdeaConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To methyl 5-bromo-3-iodobenzoate (Step A above) (5.01 g, 0.015 mole) in anhydrous methylene chloride (100 mL) at -78° C., was added dropwise minutes, diisobutylaluminum hydride (5.50 mL, 0.03 mole). The mixture was stirred for 1 hour then allowed to warm to 0° C. The reaction solution was poured into 600 mL, chilled 3N HCl and extracted 3× with methylene chloride (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield 5-bromo-3-iodobenzyl alcohol (4.54 g) as a white solid. MP=110-112° C. MS and NMR were consistent with the desired structure. The reaction solution was poured into 600 mL extracted 3× with methylene chloride (150 mL) dried over MgSO4 concentrated under vacuum
Source ID: ord-7a3136ee0bb84c16864a250cede4929fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (3-bromo-5-iodophenyl)methanol from the previous step (1.0 eq.) and Dess-Martin periodinane (1.18 eq.) was stirred at RT in dichloromethane (0.1 M) for 45 min. The reaction mixture was diluted with ether, filtered through a plug of SiO2, and the silica washed with a 3:1 (v/v) mixture of hexanes:EtOAc. The filtrate was concentrated in vacuo and passed again through a plug of SiO2, eluting with a 3:1 (v/v) mixture of hexanes:EtOAc to afford the title compound as a light yellow solid. filtered through a plug of SiO2 the silica washed with a 3:1 (v/v) mixture of hexanes The filtrate was concentrated in vacuo eluting with a 3:1 (v/v) mixture of hexanes
Source ID: ord-6897acc0ca1c4392a1990ff1b4fc9573Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromo-5-iodobenzoic acid (1.0 eq.) in THF (0.2 M) at RT was added borane-methyl sulfide complex (1.5 eq). After 3 days of stirring at RT, the reaction mixture was quenched cautiously with 2 N aq. HCl and extracted with ether. The combined organic extracts were washed with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil. the reaction mixture was quenched cautiously with 2 N aq. HCl extracted with ether The combined organic extracts were washed with 1 N aq. NaOH, water and brine dried over MgSO4 filtered
Source ID: ord-d1100e98bace429eb32b1bad879614ddPubChem References
These sources are listed in the compound's public database record.
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