2-(2-Bromophenyl)-1-(4-methoxyphenyl)ethanone

Matthias Treu and Ulrich Jordis*

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163OC, A-1060 Vienna, Austria

Tel. +43 (1) 58801.15460, Fax +43(1)58801.15499, Email: [email protected]

Received: 20 December 2001 / Accepted: 8 May 2002 / Published: 24 February 2003

To anhydrous AlCl₃ (27.35 g, 205 mmol) and anisole (24.11 g, 223 mmol) in dry chloroform (300 mL) 2-bromobenzeneacetyl chloride [1] (43.4 g, 186 mmol) in dry chloroform (100 mL) was added over 30 min at 0 °C and stirred at ambient temperature for 15 h. 2 N HCl (100 mL) was added, and the mixture was extracted with CH₂Cl₂ (2 x 100 mL). The combined organic layer was washed with 2 N HCl (2 x 250 mL), water (2 x 250 mL), satd. NaHCO₃ (2 x 200 mL) and brine (200 mL), dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was recrystallized from MeOH (50 mL). Yield: colorless crystals (51.3 g, 90%), mp. 87.5 - 88.5 °C.

TLC: petroleum ether : EtOAc = 80 : 20, R_f = 0.3.

Anal. Calcd for C₁₅H₃₁BrO: C, 59.04; H, 4.29. Found: C, 58.98; H, 4.33.

¹H NMR (CDCl₃): d 8.04 (d, J = 9.5 Hz, 2H), 7.60 (d, J = 9.5 Hz, 1H), 7.32 - 7.10 (m, 5H), 6.97 (d, J = 9.5 Hz, 2H), 4.40 (s, 2H), 3.88 (s, 3H).

¹³C NMR (CDCl₃): d 194.8 (s), 163.6 (s), 135.2 (s), 132.6 (d), 131.6 (d), 130.6 (d), 129.6 (s), 128.5 (d), 127.4 (d), 125.0 (s), 113.8 (d), 55.4 (q), 45.3 (t).

References and Notes

1. Lee, S.; Frescas, S. P.; Nichols, D. E. A new, simple procedure for the preparation of 8-methoxy-2-tetralone. Synth. Commun. 1995, 25, 2775-2780.

Samples Availability: Available from the authors.

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