Synthesis
General procedure for the synthesis of 6-bromo-1,2,3,4-tetrahydro-naphthalene from 3-(4-bromobenzoyl)propionic acid: Freshly distilled chloroform (0.6 mL) was added to a screw-capped vial fitted with a magnetic stirring bar under the protection of nitrogen, and In(OAc)3 (0.0060 mmol, 1.8 mg), I2 (0.600 mmol, 152 mg), 3 -(4-bromobenzoyl)propionic acid (0.6 mmol) and Me2PhSiH (3.90 mmol, 600 μL). The vial was sealed with a cap with a PTFE septum. The reaction vial was heated in an oil bath and the progress of the reaction was monitored by gas chromatography (GC) and thin layer chromatography (TLC) until the carboxylic acid was completely consumed. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with 2 mL of aqueous HCl. The aqueous layer was extracted with hexane (5 mL × 3). The organic phases were combined, dried with anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane) to afford the target product 6-bromo-1,2,3,4-tetrahydro-naphthalene. If necessary, the product can be further purified by gel permeation chromatography (eluent: CHCl3).
References
[1] Chemistry Letters, 2015, vol. 44, # 11, p. 1503 - 1505
