Hydrochloric Acid → HCID 23293613, compound

Participants

Reaction Steps

To a stirred, chilled (dry ice-acetone bath) solution of diisopropylamine (0.3 mL, 1.9 mmol, Aldrich) in tetrahydrofuran (3 mL) under nitrogen was successively added 2.5N n-butyl lithium in hexane (0.8 mL, Aldrich), chlorotrimethylsilane (0.2 mL, 1.8 mmol, Aldrich) and ethyl 2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthyl)acetate (236 mg, 1.0 mmol). The resulting clear solution was stirred for 1 h, treated with N-bromosuccinimide (180 mg, 1.0 mmol, Aldrich) and stirred for an additional 0.5 h before the dry ice-acetone bath was removed. The reddish cloudy solution was stirred for 2 h at room temperature, treated with dilute aq hydrochloric acid (4 meq) and extracted with diethyl ether (30 mL). The ether layer was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and chromatographed on Silica Gel 60 using dichloromethane-hexane (1:9) as eluent. Fractions containing only ethyl 2-bromo-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthyl)acetate as a 1:4 isomeric mixture were combined and concentrated in vacuo to a clear oil (171 mg, 54%); NMR (DMSO-d6): d 7.00-7.18 (m, 3H, Ar), 5.20 (d, J=6.2 Hz, 0.8H, BrCHCO), 5.17 (d, J=6.2 Hz, 0.2H, BrCHCO), 4.19 (q, 1.6H, CH2OOC), 4.14 (q, 0.4H, CH2OOC), 3.49 (m, 1H, ArCH), 2.69 (m, 2H, ArCH2), 1.81-1.97 (m, 3H, CH, CH2), 1.61-1.67 (m, 1H, CH), 1.21 (t, 2.4H, CH3), 1.07 (t, 0.6H, CH3).

Provenance & Evidence