Hydrochloric Acid → (5-Chlorobenzo[b]thiophen-2-yl)boronic acid

HRID 270009Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[Li]CCCC.CCCCCC.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][C:7]([B:22]([OH:27])[OH:23])=[CH:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of 5-chloro-benzo[b]thiophene (compound PRE10) (2.1 g, 12.46 mmol) in anhydrous THF (17 mL) was added dropwise at −60° C. n-BuLi 1.6M in hexane (8.55 mL, 13.69 mmol). After stirring for 30 min at −60° C., was added dropwise triisopropyl borate (3.17 mL, 13.69 mmol). The cooling bath was taken off and the reaction mixture was heated slowly to 0° C. and was added 1N HCl (30 mL) and ethyl acetate (30 mL). The organic layer was dried over Na2SO4 and concentrated to give 2.15 g of compound dd (white powder;

Workup

temperaturethe reaction mixture was heated slowly to 0° C.
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-310b8d1f3cc24fc285346b5f24d6bc22
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449481B2

Reaction notes

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