HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Bromo-4-(trifluoromethoxy)benzaldehyde → 3-(5-Hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Bromo-4-(trifluoromethoxy)benzaldehyde | HCID 13150416 | — |
| Reactant | [3,3-Dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-methanol | HCID 18445402 | — |
| Product | 3-(5-Hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde | HCID 18445409 | 59% |
Reaction Steps
The intermediate 3-(5-hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde was prepared in a similar manner to example 1a using [3,3-dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-methanol and 3-bromo-4-trifluoromethoxy benzaldehyde. 59% yield. 1H-NMR (300 MHz, CDCl3): 1.39 (s, 6H), 1.71 (m, 1H), 4.26 (s, 2H), 4.68 (s, 2H), 7.14 (d, J=2.3 Hz, 1H), 7.21 (d, J=1.5 Hz, 1H), 7.49 (dd, J1=8.5 Hz, J2=1.5 Hz, 1H), 7.91 (dd, J1=8.5 Hz, J2=2.1 Hz, 1H), 8.01 (d, J=2.3 Hz, 1H), 10.03 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07196108B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-2445a4763310420490e249d0bd62c384 |
| Source note | uspto-grants-2007_03 |