Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67053845 | HCID 67053845 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67053925 | HCID 67053925 | 75.8% |
Reaction Steps
To a solution of 6-fluoro-5-methoxy-1,1-dimethyl-indan (1.40 g, 7.21 mmol) in 20.0 ml of DCM at −78° C. was added BBr3 (1.40 ml, 14.4 mmol) in DCM (10.0 ml). The reaction mixture was stirred at −78° C. for two hours before being treated with 2.0 ml of methanol. This mixture was stirred for few minutes after which a saturated solution of NaHCO3 was carefully added and the resulting mixture stirred for an additional 1 hour. The mixture was extracted with DCM (3×40 mL) and the combined organic extracts were washed with brine and dried over Na2SO4. Flash column chromatography on silica gel (2-10% ethyl acetate/heptanes) afforded 0.985 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051331B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-d4c8b61f256b45b0a5750480f0aea142 |
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| Source note | uspto-grants-2015_06 |
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