Hydrochloric Acid → B-(6-chloro-2-naphthalenyl)Boronic acid

HRID 1817755Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([B:12]1[O:16]C(C)(C)C(C)(C)[O:13]1)[CH:6]=[CH:5]2.Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([B:12]([OH:16])[OH:13])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

2-(6-Chloro-2-naphthyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (340 mg, 1.18 mmol) was suspended in a mixture of 20 mL of acetone and 5 mL of aqueous 2N hydrochloric acid and heated at 50° C. for 16 h. The product was purified by reverse phase HPLC to provide the title compound as a white powder. 1H NMP (500 MHz, DMSO) δ: 8.38 (s, 1H); 8.23 (s, 2H); 8.01 (d, J=2.1 Hz, 1H); 7.95 (d, J=8.7 Hz, 1H); 7.91 (d, 8.2 Hz, 1H); 7.84 (d, J=8.2 Hz, 1H); 7.50 (dd, J=2.3, 8.7 Hz, 1H).

Workup

customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-450622d6b19c419a8454c7a3b5e6b63d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598285B2

Reaction notes

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