6-Bromo-1,2,3,4-tetrahydronaphthalene

General procedure: Freshly distilled chloroform (0.6 mL)was placed into a screw-capped vial under N2, and a magnetic stirrer bar, In(OAc)3(0.0060 mmol, 1.8 mg), I2 (0.600 mmol, 152 mg), a carboxylic acid (0.6 mmol), andMe2PhSiH (3.90 mmol, 600 μL) were successively added. The vial was sealed with acap that contained a PTFE septum. The reaction vial was heated in an oil bath, and thereaction was monitored by GC and TLC until the ester had been completely consumed.After the reaction was complete, the mixture was cooled to room temperature, and wasquenched with HCl aqueous solution (2 mL). The aqueous layer was extracted withhexane (5 mL x 3). The combined organic phases were dried with anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purifiedby silica gel column chromatography (hexane) to give the corresponding tetralinderivatives. If necessary, further purification was performed by gel permeationchromatography (eluent: CHCl3).(2)EXAMPLE II-18 Step 1 : 2-Bromo-5, 6, 7, 8-tetrahydronaphthaleneTo aluminum oxide (neutral Brockman grade 1) (8 g) was added 1, 2, 3, 4- tetrahydronaphthalene (1.06g, 8mmol). The mixture was stirred to give a homogeneous mixture. To this mixture was added over 5 minutes a mixture of bromine (1.44g, 9mmol) on alumina (8g). After stirring for another 5 minutes the mixture was added to a plug of silica gel was washed with methylene chloride (200ml). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100percent heptane to give the title compound containing some starting material (0.65g, 42percent).

Molecular Weight:211.10
XLogP3:4
Exact Mass:210.00441
Monoisotopic Mass:210.00441
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes