HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-bromobutanimide → 6-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 1,1'-Azobis(cyclohexanecarbonitrile) | HCID 74978 | — |
| Reactant | Ethyl 2-((tert-butyldimethylsilyl)oxy)-6-methylbenzoate | HCID 69585527 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Product | 6-Bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester | HCID 69585518 | 83.1% |
Reaction Steps
2-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid ethyl ester (7.6 g, 25.8 mmol), N-bromosuccinimide (4.82 g, 27.1 mmol) and azobis(cyclohexanecarbonitrile) (0.32 g, 13 mmol) were dissolved in tetrachlormethane (130 ml). The solution was stirred at room temperature for 60 hours. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel column using a gradient of 1–2% ethyl acetate/hexane as eluent, which afforded 8.0 g (83%) of 6-bromomethyl-2-(tert-butyl-dimethyl-silanyloxy)-benzoic acid ethyl ester as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115624B1 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-13122a0b7af2436393312ec0f0eaeeef |
| Source note | uspto-grants-2006_10 |