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CCOC(C1=CC(=CO1)Br)OCCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromo-2-(diethoxymethyl)furan |
|---|---|
| IUPAC Name | — |
| CAS Number | 27065-51-6 |
| Database ID | 13995070 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromo-2-(diethoxymethyl)furan (CAS 27065-51-6) 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 13995070
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-53052d299930471b92d480b9d9e25862Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c00e8e501d904a90bf4ca9417ccb6d9eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-53052d299930471b92d480b9d9e25862Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared according to procedure B from 4,4-dimethyl 2 oxo-1,4-dihydro 2H-benzo[d][1,3]oxazin-6-boronic acid and 3-bromo-5-Diethoxymethyl furan. A brown gum: 1H NMR (DMSO-d6) δ 10.2 (s, 1H), 8.12 (s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88 (m, 2H), 5.56 (s, 1H), 3.60-3.38 (m, 4H), 1.67 (s, 6H), 1.2-1.14 (m, 6H). MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO5.1/2 H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78. Prepared
Source ID: ord-2fa0d45d13e846aaa60c6b6a49c8ea2bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c00e8e501d904a90bf4ca9417ccb6d9eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared according to procedure B from 4,4-dimethyl 2 oxo-1,4-dihydro 2H-benzo[d][1,3]oxazin-6-boronic acid and 3-bromo-5-Diethoxymethyl furan. A brown gum: 1H NMR (DMSO-d6) δ 10.2 (s, 1H), 8.12 (s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88 (m, 2H), 5.56 (s, 1H), 3.60-3.38 (m, 4H), 1.67 (s, 6H), 1.2-1.14 (m, 6H). MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO5.1/2 H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78. Prepared
Source ID: ord-2fa0d45d13e846aaa60c6b6a49c8ea2bConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: An amount of 1.0 g (4.1 mmol) of 4-bromo-2-(diethoxymethyl)furan, is dissolved in ether (15 mL) and cooled to −78° C. To this is added 4.3 mL (6.02 mmol) of sec-butyllithium. After stirring at −78° C. for 30 minutes, triisopropyl borate (1.10 mL, 5.01 mmol) is added dropwise. The mixture is stirred at −78° C. for 1.5 hours and brought to room temperature for 2 hours. The mixture is hydrolyzed with 2N HCl and stirred at room temperature for 1 hour. The ether layer is separated and the water layer is washed once more with ether. The combined ether layers is washed once with brine and dried with sodium sulfate. Evaporated to give 563 mg of the boronic acid as dark oil. The mixture is stirred at −78° C. for 1.5 hours brought to room temperature for 2 hours stirred at room temperature for 1 hour The ether layer is separated the water layer is washed once more with ether The combined ether layers is washed once with brine dried with sodium sulfate Evaporated
Source ID: ord-4bcd197f139740dab06f6230d46a218dConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: An amount of 1.0 g (4.1 mmol) of 4-bromo-2-(diethoxymethyl)furan, is dissolved in ether (15 mL) and cooled to −78° C. To this is added 4.3 mL (6.02 mmol) of sec-butyllithium. After stirring at −78° C. for 30 minutes, triisopropyl borate (1.10 mL, 5.01 mmol) is added dropwise. The mixture is stirred at −78° C. for 1.5 hours and brought to room temperature for 2 hours. The mixture is hydrolyzed with 2N HCl and stirred at room temperature for 1 hour. The ether layer is separated and the water layer is washed once more with ether. The combined ether layers is washed once with brine and dried with sodium sulfate. Evaporated to give 563 mg of the boronic acid as dark oil. The mixture is stirred at −78° C. for 1.5 hours brought to room temperature for 2 hours stirred at room temperature for 1 hour The ether layer is separated the water layer is washed once more with ether The combined ether layers is washed once with brine dried with sodium sulfate Evaporated
Source ID: ord-4bcd197f139740dab06f6230d46a218dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared according to procedure B from 4,4-dimethyl 2 oxo -1,4-dihydro 2H-benzo[d][1,3]oxazine-6-boronic acid and 3-bromo-5-diethoxymehyl furan. A brown gum: 1H NMR (DMSO-d6) δ10.2 (s, 1H), 8.12(s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88(m, 2H), 5.56(s, 1H), 3.60-3.38(m, 4H), 1.67(s ,6H), 1.2-1.14 (m, 6H). .MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO51/2 H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78. Prepared
Source ID: ord-4e258a52c8374abb99bcb4f082793adbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-(2,4-dichloro-5-methoxyanilino)-7-iodo-6-methoxy-3-quinolinecarbonitrile (3.5 g, 7.00 mmol), tributyl [5-(diethoxymethyl)-3-furanyl]stannane (generated from reaction of 4-bromo-2-(diethoxymethyl)-furan [ref. Chiarello, J, Joullie, M. M., Tetrahedron, 44(1), 41-48 (1988)] with tributyl tin chloride in the presence of n-BuLi) (5.76 g, 12.55 mmol), and dichlorobis(triphenylphosphine)pallidium (II) (100 mg) in 80 mL of dioxane is heated at reflux for 5 hours. Additional dichlorobis(triphenylphosphine)pallidium (II) (100 mg) is added and the reaction mixture is heated at reflux overnight. The reaction mixture is partitioned between ethyl acetate and water. The insoluble material is collected by filtration to provide 1.09 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-[5-(diethoxymethyl)-3-furyl]-6-methoxy-3-quinolinecarbonitrile as a pale green solid; 1H NMR (DMSO-d6) δ 1.18 (t, J=7 Hz, 6H), 3.63 (q, J=7 Hz, 4H), 3.87 (s, 3H), 4.07 (s, 3H), 5.60 (s, 1H), 7.13 (s, 1H), 7.37 (s, 1H), 7.76 (s, 1H), 7.95 (s, 1H), 8.15 (s, 1H), 8.35 (s, 1H), 8.45 (s, 1H), 9.84 (s, 1H); MS 542.1, 544.1 (M+H)+. is heated at reflux for 5 hours the reaction mixture is heated at reflux overnight The reaction mixture is partitioned between ethyl acetate and water The insoluble material is collected by filtration
Source ID: ord-81d488b5e15d4bd794d426361ea9e401Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared according to procedure B from 4,4-dimethyl 2 oxo-1,4-dihydro 2 H-benzo [d][1,3]oxazine -6-boronic acid and 3-bromo-5-diethoxymethyl furan. A brown gum: 1H NMR (DMSO-d6) δ10.2 (s, 1H), 8.12(s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88(m, 2H), 5.56(s, 1H), 3.60-3.38(m, 4H), 1.67(s ,6H), 1.2-1.14 (m, 6H). MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO5.½ H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78. Prepared
Source ID: ord-b0ee819d8a53411491aaef9adeb11d0dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared according to procedure B from 4,4-dimethyl 2 oxo-1,4-dihydro 2H-benzo[d][1,3]oxazin-6-boronic acid and 3-bromo-5-Diethoxymethyl furan. A brown gum: 1H NMR (DMSO-d6) δ 10.2 (s, 1H), 8.12 (s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88 (m, 2H), 5.56 (s, 1H), 3.60-3.38 (m, 4H), 1.67 (s, 6H), 1.2-1.14 (m, 6H). MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO5.1/2 H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78. Prepared
Source ID: ord-2fa0d45d13e846aaa60c6b6a49c8ea2bPubChem References
These sources are listed in the compound's public database record.
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