Sodium Hydroxide → 4-(3-Bromophenyl)butan-1-ol

Beteiligte Stoffe

Reaktionsschritte

A cold (0° C.) solution of 4-(3-bromophenyl)butyric acid (2.85 g, 11.7 mmol) in THF was treated slowly with a solution of B2H6-THF (35 mL), stirred at room temperature for 18 hours, poured into ice/water, basified with 2.5 N NaOH to pH=11 and extracted with CH2Cl2. The extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by column chromatography using hexanes/CH2Cl2/MeOH (4/4.5/0.5) as the eluting solvent afforded 4-(3-bromophenyl)butan-1-ol as a colorless oil (1.9 g, 70% yield. m/e (M)+ 228; 1H NMR (400 MHZ, DMSO-d6) δ ppm, 1.3-1.4 (m, 2 H) 1.5-1.6 (m, 2 H), 2.55-2.59 (m, 2 H), 3.3-3.38 (m, 2H), 4.3 (t, J=7.5, 1H), 7.2-7.2 (m, 1 H), 7.3 (t, J=7.5 Hz, 1 H), 7.4-7.4 (m, 1 H), 7.4-7.4 (m, 1 H).

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