2-Bromo-5-hydroxy-4-methoxybenzenemethanol

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 2-bromo-5-hydroxy-4-methoxybenzaldehyde [1] (60.0 g, 260 mmol) in dry EtOH (500 mL) NaBH₄ (20.0 g, 529 mmol) was added at 15 °C within 20 min and stirred for 18 h at ambient temperature. The mixture was concentrated in vacuo, the residue was treated with satd. NaHCO₃ (500 mL) and extracted with Et₂O (3 x 150 mL). The combined organic layer was washed with satd. NaHCO₃ (3 x 250 mL) and brine (400 mL), dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was recrystallized from iPr₂O (100 mL). Yield: offwhite crystals (39.85 g, 66%), mp. 115 - 117 °C.

TLC: petroleum ether : EtOAc = 90 : 10, R_f = 0.1.

Anal. Calcd for C₈H₉BrO₃: C, 41.23; H, 3.89. Found: C, 41.13; H, 3.75.

¹H NMR (CDCl₃). d 7.05 (s, 1H), 6.95 (s, 1H), 4.65 (s, 2H), 3.90 (s, 3H).

¹³C NMR (CDCl₃). d 146.5 (s), 145.2 (s), 132.7 (s), 115.3 (s), 114.9 (d), 111.6 (d), 64.8 (t), 56.3 (q).

References and Notes

1. Commercially available from FLUKA.

Samples Availability: Available from the authors.

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