Hydrochloric Acid → 3,4-Dihydronaphthalen-2-ylboronic acid
Reaction equation
Br[C:2]1[CH2:3][CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])(C)(C)C.C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C.Cl>C(OCC)C.CCCCC>[CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[B:21]([OH:22])[OH:20]Participants
7
Conditions
- Temperature
- -65 °C
Procedure
A solution of 3-bromo-1,2-dihydro-naphthalene (7.7 g, 37 mmol) (Adamczyk, M.; Watt, D. S.; Netzel, D. A. J. Org. Chem. 1984, 49, 4226-4237) in diethylether (370 ml) was cooled in a dry ice bath and tert.-butyllithium solution (50 ml of a 1.5 M solution in pentane) was added maintaining T<−65° C. At this temperature stirring was continued for 30 min, then triisopropylborate (17.3 ml, 75 mmol) was added. The reaction mixture was brought to rt and treated with 3N HCl (100 ml). After 15 min the organic phase was dried (Na2SO4), evaporated and precipitated with pentane to provide the title compound (3.83 g, 60%) as a white solid material. MS: m/e=173 (M−H−).
Workup
- customwas brought to rt
- dry with materialAfter 15 min the organic phase was dried (Na2SO4)
- customevaporated
- customprecipitated with pentane
Sources & evidence
- ORD record
- ord-ca0f343ecd7f41c3a9b6ca562240cf91
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07005432B2
Reaction notes
Loading…