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ChemicalBook CAS DataBase List 4-Bromobutylboronic acid
61632-72-2

4-Bromobutylboronic acid synthesis

5synthesis methods
-

Yield: 78%

Reaction Conditions:

with benzo[1,3,2]dioxaborole in water

Steps:

A 4-Bromobutyl boronic acid
EXAMPLE A 4-Bromobutyl boronic acid 4-Bromo-1-butene (5.4 g, 40 mmol) was added to catecholborane (5.76 g, 48 mmol). The reaction mixture was stirred under nitrogen and heated to 95° C. for 4 hours. The unreacted starting material was distilled under high vacuum (1 mm Hg) at room temperature. Water (70 mL) was added to the slightly yellow liquid residue and stirred for 2 hours. The white solid was filtered and recrystallized from chloroform. Crystals (5.6 g) were obtained and were used in the next step without further purification. Yield 78%; mp 81°-83° C.; 1 H NMR (DMSO-d6) 0.58-0.67 (t, B CH2), 1.40-1.52 (m, B CH2 CH2), 1.61-1.85 (m, CH2 CH2 Br), 3.48-3.58 (t, CH2 CH2 Br), 7.40-7.48 (s, (HO)2 B).

References:

Macronex, Inc.;University of North Carolina US5643893, 1997, A