Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | HCID 68648457 | HCID 68648457 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68281404 | HCID 68281404 | 93.2% |
Reaction Steps
Dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terephthalate (CVI) (2.60 g, 8.12 mmol) was dissolved in DCM (25 mL), flushed with argon and cooled to −10° C. A 1 M solution of diisobutylaluminum hydride in DCM (48.73 mL, 48.73 mmol) was then added dropwise and the reaction was stirred at 0° C. for 2 h. 1 N aqueous HCl (50 mL) was carefully added and stirred for 5 minutes. The reaction was extracted with DCM and the combined extracts were washed with brine, dried over anhydrous MgSO4 and concentrated to give (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-phenylene)dimethanol (CVII) (2.0 g, 7.57 mmol). The crude product was used without further purification for step 4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933018B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-284cb6e3e9cc48d89a3c75950c7e7dbc |
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| Source note | uspto-grants-2015_01 |
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