Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (5-Bromo-2-chlorophenyl)methanol | HCID 5074766 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58007486 | HCID 58007486 | 96.4% |
Reaction Steps
TBDMS-Cl (10.6 g, 66.7 mmol) was added to a sol. of (5-bromo-2-chloro-phenyl)-methanol (12.8 g, 55.6 mmol) and imidazole (9.42 g, 138 mmol) in DMF (190 mL) at 0° C. The mixture was stirred for 2 h at 0° C., and aq. sat. NH4Cl was added. The mixture was extracted with heptane (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane→EtOAc/heptane 1:49) yielded the title compound (18.0 g, 96%). LC-MS: tR=1.22 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968720B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-5b2b22c7580f4b51935cbb5e0d14a47f |
|---|
| Source note | uspto-grants-2011_06 |
|---|