2-Bromophenol → HCID 20090600, compound

Participants

Reaction Steps

2-Bromophenol (1.50 g., 8.70 mmol) is alkylated with 2-chloromethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene) (18a) (2.05 g., 8.70 mmol) in a similar manner as described in Example 26 (for the synthesis of 44) to afford 2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy-bromobenzene (50) (2.88 g., 7.72 mmol, 89%): chromatographed on silica gel using EtOAc/hexane to afford a clear oil; 1H NMR (300 MHz, CDCl3) δ 7.57 (dd, J=2, 8 Hz, 1H, ArH), 7.45 (d, J=2 Hz, 1H, ArH), 7.32 (d, J=8 Hz, 1H, ArH), 7.25 (m, 2H, ArH, 6.98 (dd, J=2, 8 Hz, 1H, ArH), 6.83 (dd, J=8, 8 Hz, 1H, ArH), 5.09 (s, 2H, ArCH2O), 1.70 (s, 4H, CH2CH2), 1.29 (s, 6H, 2×CH3), 1.28 (s, 6H, 2×CH3) .

Provenance & Evidence