Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 2-Chlorobenzoxazole | HCID 11986 | — |
| Reactant | (4-Bromophenoxy)(tert-butyl)dimethylsilane | HCID 4227167 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(Benzo[d]oxazol-2-yl)phenol | HCID 2785587 | — |
Reaction Steps
To a solution of 4-bromo-t-butyldimethylsilyloxybenzene (8.3 g; 29 mmol) in THF (60 ml) at -78° C. is added a solution of butyllithium in hexane (14 ml; 35 mmol) over 10 minutes. This is allowed to stir 1 hour and 2-chlorobenzoxazole (4 ml; 35 mmol) is added dropwise over 5 minutes. After stirring 15 minutes, the reaction is allowed to warm to 0° C. and is quenched with MeOH. This is then poured into 1N HCl and after stirring 1 hour is extracted with ethyl acetate. The organic extracts are dried (MgSO4) and then concentrated to yield 4-(benzoxazol-2-yl)phenol which is used directly in Step C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05561143 |
|---|
| Source dataset | uspto-grants-1996_10 |
|---|
| ORD ID | ord-b5bae37e7d8c4b23aa935656c6e98a25 |
|---|
| Source note | uspto-grants-1996_10 |
|---|
